Design and synthesis of novel type VI-like β-turn mimetics. Diversity at the i+1 and the i+2 position
In this paper, a synthetic approach for functionalised 5-aminopiperidinone-2-carboxylate (APC) systems as non-pro cis-peptide bond containing external β-turn mimics is presented. The scope and limitations of the synthetic method are discussed and the potential turn inducing properties of a model com...
Saved in:
Published in | Tetrahedron Vol. 60; no. 50; pp. 11597 - 11612 |
---|---|
Main Authors | , , , , , , , , , |
Format | Journal Article |
Language | English |
Published |
OXFORD
Elsevier Ltd
06.12.2004
Elsevier |
Subjects | |
Online Access | Get full text |
Cover
Loading…
Abstract | In this paper, a synthetic approach for functionalised 5-aminopiperidinone-2-carboxylate (APC) systems as non-pro
cis-peptide bond containing external β-turn mimics is presented. The scope and limitations of the synthetic method are discussed and the potential turn inducing properties of a model compound are evaluated by means of molecular modelling and NMR analysis.
Graphical Abstract |
---|---|
AbstractList | In this paper, a synthetic approach for functionalised 5-aminopiperidinone-2-carboxylate (APC) systems as non-pro
cis-peptide bond containing external β-turn mimics is presented. The scope and limitations of the synthetic method are discussed and the potential turn inducing properties of a model compound are evaluated by means of molecular modelling and NMR analysis.
Graphical Abstract In this paper, a synthetic approach for functionalised 5-aminopiperidinone-2-carboxylate (APC) systems as non-pro cis-peptide bond containing external beta-turn mimics is presented. The scope and limitations of the synthetic method are discussed and the potential turn inducing properties of a model compound are evaluated by means of molecular modelling and NMR analysis. (C) 2004 Elsevier Ltd. All rights reserved. |
Author | Rombouts, Frederik J.R. Pawar, Vijaykumar G. De Borggraeve, Wim M. Kamoune, Laila Alen, Jo Hoornaert, Georges J. Compernolle, Frans Verbist, Bie M.P. Smets, Wim J. Van der Eycken, Erik V. |
Author_xml | – sequence: 1 givenname: Wim M. surname: De Borggraeve fullname: De Borggraeve, Wim M. email: wim.deborggraeve@chem.kuleuven.ac.be – sequence: 2 givenname: Bie M.P. surname: Verbist fullname: Verbist, Bie M.P. – sequence: 3 givenname: Frederik J.R. surname: Rombouts fullname: Rombouts, Frederik J.R. – sequence: 4 givenname: Vijaykumar G. surname: Pawar fullname: Pawar, Vijaykumar G. – sequence: 5 givenname: Wim J. surname: Smets fullname: Smets, Wim J. – sequence: 6 givenname: Laila surname: Kamoune fullname: Kamoune, Laila – sequence: 7 givenname: Jo surname: Alen fullname: Alen, Jo – sequence: 8 givenname: Erik V. surname: Van der Eycken fullname: Van der Eycken, Erik V. – sequence: 9 givenname: Frans surname: Compernolle fullname: Compernolle, Frans – sequence: 10 givenname: Georges J. surname: Hoornaert fullname: Hoornaert, Georges J. |
BookMark | eNqNkEtOwzAQQC1UJNrCAdh5XyXYjpM0YoVaPpUqsQG2luOMwaW1q9gtyrU4CGfCJRVLxMpjzbz5vBEaWGcBoUtKUkpocbVKA4SUEcJTUqUk5ydoSHnBk5zTYoCGMUESThg5QyPvV4QQSlk2RHoO3rxaLG2DfWfDW_x67DS2bg9rHLot4JdFsjbvgL8-k7BrLd6YDQSjfIrnZg-tN6HDMuDIYjOhP636mOGti1nj7Dk61XLt4eL4jtHz3e3T7CFZPt4vZjfLRLEqDwkvdKnzTOcAKt5QccZyyCBXZaVBskqVRZ2xmhMFStaFLFWTM11LKqeZamiRjRHt-6rWed-CFtvWbGTbCUrEQZRYiShKHEQJUok4JDLTnvmA2mmvDFgFv1w0FZegfBoDktGZCfJw0MztbIjo5P9orL7uqyEa2BtoxZFoTAsqiMaZP9b8BszrlHw |
CitedBy_id | crossref_primary_10_1002_ejoc_200600805 crossref_primary_10_1016_j_tet_2009_01_057 crossref_primary_10_1016_j_tet_2008_06_056 crossref_primary_10_1107_S1600536807063441 crossref_primary_10_1002_bip_20382 crossref_primary_10_1016_j_tet_2018_01_005 crossref_primary_10_1002_ejoc_200500996 crossref_primary_10_1016_j_tetlet_2005_01_056 crossref_primary_10_1016_j_tetlet_2014_06_100 crossref_primary_10_1021_jo062176a crossref_primary_10_1002_ejoc_200500036 crossref_primary_10_1016_j_tetlet_2006_05_181 crossref_primary_10_1556_JFC_D_14_00036 crossref_primary_10_1016_j_crci_2008_09_004 crossref_primary_10_1016_j_tetlet_2012_06_080 crossref_primary_10_1039_b905501k crossref_primary_10_1107_S1600536811012165 crossref_primary_10_1016_j_tet_2005_07_085 crossref_primary_10_1039_D2RA07227K crossref_primary_10_1021_jo4003163 crossref_primary_10_1039_C6OB02358D |
Cites_doi | 10.1021/jo0263216 10.1021/cc0300098 10.1006/abio.2000.4757 10.1016/S0040-4020(03)00826-3 10.1016/j.tetlet.2004.03.186 10.1016/j.tetlet.2004.01.017 10.1002/ejoc.200200652 10.1016/S0040-4020(03)00741-5 10.1016/S0040-4020(03)00732-4 10.1016/S0040-4039(00)87700-X 10.1006/jmbi.1998.2459 10.1021/jo00186a042 10.1002/recl.19941130102 10.1016/S0040-4039(01)01080-2 10.2174/0929867003374499 10.1038/1368 10.1016/S0040-4039(01)02188-8 10.1023/B:MODI.0000006807.43408.d5 10.1016/S0040-4020(98)00802-3 10.1021/ol049979+ 10.1016/S0040-4039(00)76740-2 10.1002/jcc.540110405 10.1016/S0040-4039(00)87699-6 10.1021/jo960012w 10.1002/jhet.5570200414 10.1016/0040-4020(95)00802-F 10.1016/S0040-4020(97)00298-6 10.1016/S0040-4020(01)90216-9 10.1016/S0040-4039(00)75983-1 10.1021/ja970855k 10.1016/S0040-4020(01)90207-8 10.1016/S0040-4039(01)01545-3 10.1002/jmr.300030202 10.1039/p19960000231 |
ContentType | Journal Article |
Copyright | 2004 Elsevier Ltd |
Copyright_xml | – notice: 2004 Elsevier Ltd |
DBID | 1KM BLEPL DTL FYDSC AAYXX CITATION |
DOI | 10.1016/j.tet.2004.09.054 |
DatabaseName | Index Chemicus Web of Science Core Collection Science Citation Index Expanded Web of Science - Science Citation Index Expanded - 2004 CrossRef |
DatabaseTitle | Web of Science CrossRef |
DatabaseTitleList | Web of Science |
Database_xml | – sequence: 1 dbid: 1KM name: Index Chemicus url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/woscc/search-with-editions?editions=WOS.IC sourceTypes: Enrichment Source Index Database |
DeliveryMethod | fulltext_linktorsrc |
Discipline | Chemistry |
EISSN | 1464-5416 |
EndPage | 11612 |
ExternalDocumentID | 10_1016_j_tet_2004_09_054 000225148000031 S0040402004015777 |
GroupedDBID | --- --K --M -DZ -ET -~X .GJ .~1 0R~ 123 186 1B1 1RT 1~. 1~5 29Q 4.4 457 4G. 53G 5RE 5VS 6TJ 7-5 71M 8P~ 9JM 9JN AABNK AACTN AAEDT AAEDW AAIAV AAIKC AAIKJ AAKOC AALRI AAMNW AAOAW AAQFI AAQXK AARLI AATCM AAXUO AAYJJ ABEFU ABFNM ABGSF ABJNI ABMAC ABPPZ ABUDA ABXDB ABYKQ ABZDS ACBNA ACDAQ ACGFS ACKIV ACNCT ACNNM ACRLP ADBBV ADECG ADEZE ADMUD ADUVX AEBSH AEHWI AEKER AENEX AETEA AFFNX AFKWA AFMIJ AFTJW AFXIZ AFZHZ AGHFR AGRDE AGUBO AGYEJ AHHHB AIEXJ AIKHN AITUG AJBFU AJOXV AJSZI ALCLG ALMA_UNASSIGNED_HOLDINGS AMFUW AMRAJ ASPBG AVWKF AXJTR AZFZN BKOJK BLXMC CS3 DOVZS DU5 EBS EFJIC EFLBG EJD EO8 EO9 EP2 EP3 F5P FDB FEDTE FGOYB FIRID FLBIZ FNPLU FYGXN G-Q G8K GBLVA HMS HVGLF HZ~ IHE J1W K-O KOM M2Z M41 MO0 MVM N9A NEJ O-L O9- OAUVE OGGZJ OHT OZT P-8 P-9 P2P PC. PVJ Q38 R2- RIG RNS ROL RPZ SCB SCC SDF SDG SDP SES SEW SOC SPC SPCBC SSK SSP SSU T5K TN5 TWZ UQL WH7 WUQ XFK XOL XPP XSW YK3 YR2 ZCG ZKB ZMT ~G- 1KM AAHBH AAXKI ADVLN AKRWK BLEPL DTL GROUPED_WOS_SCIENCE_CITATION_INDEX_EXPANDED AAYXX AFJKZ CITATION |
ID | FETCH-LOGICAL-c295t-46f7f53f5eec05494225e3e5c79fea29c76b32b40cecab6a7cd52fba1a83cd163 |
IEDL.DBID | AIKHN |
ISICitedReferencesCount | 23 |
ISICitedReferencesURI | https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=000225148000031 |
ISSN | 0040-4020 |
IngestDate | Thu Sep 26 17:36:37 EDT 2024 Tue Sep 17 22:32:09 EDT 2024 Fri Oct 04 21:02:34 EDT 2024 Fri Feb 23 02:23:44 EST 2024 |
IsPeerReviewed | true |
IsScholarly | true |
Issue | 50 |
Keywords | Diels–Alder reaction Turn mimics Pyrazinone PEPTIDE-BONDS DIELS-ALDER REACTIONS turn mimics POLYPEPTIDES STABILIZE SECONDARY STRUCTURES GLY-PRO AMINO-ACIDS pyrazinone 2(1H)-PYRAZINONES GENERATION Diels-Alder reaction CONFORMATIONAL-ANALYSIS DERIVATIVES |
Language | English |
LinkModel | DirectLink |
LogoURL | https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg |
MergedId | FETCHMERGED-LOGICAL-c295t-46f7f53f5eec05494225e3e5c79fea29c76b32b40cecab6a7cd52fba1a83cd163 |
ORCID | 0000-0001-7813-6192 0000-0001-5172-7208 |
PageCount | 16 |
ParticipantIDs | webofscience_primary_000225148000031CitationCount elsevier_sciencedirect_doi_10_1016_j_tet_2004_09_054 crossref_primary_10_1016_j_tet_2004_09_054 webofscience_primary_000225148000031 |
PublicationCentury | 2000 |
PublicationDate | 2004-12-06 |
PublicationDateYYYYMMDD | 2004-12-06 |
PublicationDate_xml | – month: 12 year: 2004 text: 2004-12-06 day: 06 |
PublicationDecade | 2000 |
PublicationPlace | OXFORD |
PublicationPlace_xml | – name: OXFORD |
PublicationTitle | Tetrahedron |
PublicationTitleAbbrev | TETRAHEDRON |
PublicationYear | 2004 |
Publisher | Elsevier Ltd Elsevier |
Publisher_xml | – name: Elsevier Ltd – name: Elsevier |
References | Gramberg, Robinson (bib8) 1994; 35 Ball, Alewood (bib4) 1990; 3 Kemp, McNamara, Kemp, McNamara, Kemp, Sun (bib6) 1982; 23 Nagai, Sato, Nakamura, Kato (bib5) 1993; 49 Rombouts, De Borggraeve, Delaere, Froeyen, Toppet, Compernolle, Hoornaert, Takeuchi, Marshall (bib9) 2003; 120 Hruby, Balse, Hanessian, McNaughtonSmith, Lombart, Lubell, Liskamp (bib3) 2000; 7 Hoye, Eklov, Ryba, Voloshin, Yao (bib23) 2004; 6 Mohamadi, Richards, Guida, Liskamp, Lipton, Caufield, Chang, Hendrickson, Still (bib10) 1990; 11 Weiss, Jabs, Hilgenfeld, Jabs, Weiss, Hilgenfeld (bib1) 1998; 5 In the publication by Marshall, another definition of the angle β is used. We took the original definition as given by Ball. bib25 Ball, Hughes, Alewood, Andrews (bib11) 1993; 49 bib24 Verbist, Smets, De Borggraeve, Compernolle, Hoornaert (bib20) 2004; 45 De Borggraeve, Rombouts, Van der Eycken, Toppet, Hoornaert (bib14) 2001; 42 Rogiers, De Borggraeve, Toppet, Compernolle, Hoornaert (bib21) 2003; 59 Van der Eycken, Appukkuttan, De Borggraeve, Dehaen, Dallinger, Kappe (bib19) 2002; 67 Azzam, De Borggraeve, Compernolle, Hoornaert, De Borggraeve, Rombouts, Verbist, Van der Eycken, Hoornaert, Rombouts, De Borggraeve, Toppet, Compernolle, Hoornaert, Rombouts, Van den Bossche, Toppet, Compernolle, Hoornaert, Govaerts, Vogels, Compernolle, Hoornaert, Tahri, Buysens, Van der Eycken, Vandenberghe, Hoornaert, Buysens, Vandenberghe, Toppet, Hoornaert, Buysens, Vandenberghe, Toppet, Hoornaert, Kaval, Van Der Eycken, Caroen, Dehaen, Strohmeier, Kappe, Van Der Eycken, Kaval, Bisztray, Dehaen, Kappe, Van der Eycken (bib15) 2004; 45 bib18 Vekemans, Pollers-Wieërs, Hoornaert (bib13) 1983; 20 bib16 bib17 Pataï (bib22) 1970 Dumas, Germanas, Kim, Dumas, Germanas (bib7) 1994; 35 Chou (bib2) 2000; 286 HOYE TR (WOS:000225148000031.13) 2004; 6 Rogiers, J (WOS:000183860800016) 2003; 59 BALL, JB (WOS:A1993LA10200004) 1993; 49 Takeuchi, Y (WOS:000074213800002) 1998; 120 VEKEMANS, J (WOS:A1983RE04100014) 1983; 20 KEMP, DS (WOS:A1982PE98500007) 1982; 23 Govaerts, TC (WOS:000184164900013) 2003; 59 Jabs, A (WOS:000078702000023) 1999; 286 MOHAMADI, F (WOS:A1990CZ22100004) 1990; 11 Tahri, A (WOS:000076290600019) 1998; 54 LISKAMP, RMJ (WOS:A1994NC25600001) 1994; 113 Verbist, BMP (WOS:000221564200039) 2004; 45 Rombouts, FJR (WOS:000183780900002) 2003; 59 PATAI S (WOS:000225148000031.25) 1970 De Borggraeve, WM (WOS:000173262000026) 2002; 43 Chou, KC (WOS:000165201200001) 2000; 286 Kim, KH (WOS:A1996UJ09400037) 1996; 61 BUYSENS, KJ (WOS:A1995TD21800027) 1995; 51 Rombouts, FJR (WOS:000171456400017) 2001; 42 Weiss, MS (WOS:000075044600009) 1998; 5 Rombouts, FJR (WOS:000183105000007) 2003; 2003 KEMP, DS (WOS:A1982PE98500006) 1982; 23 Kaval, N (WOS:000207200600005) 2003; 7 GRAMBERG, D (WOS:A1994MV16900014) 1994; 35 Azzam, R (WOS:000189116200016) 2004; 45 NAGAI, U (WOS:A1993LA10200013) 1993; 49 Van der Eycken, E (WOS:000178820200052) 2002; 67 De Borggraeve, WM (WOS:000170309700025) 2001; 42 Kaval, N (WOS:000185247200003) 2003; 5 KEMP, DS (WOS:A1984SW65900042) 1984; 49 Hanessian, S (WOS:A1997XW84000002) 1997; 53 Hruby, VJ (WOS:000088981000006) 2000; 7 DUMAS, JP (WOS:A1994MZ86100007) 1994; 35 Buysens, KJ (WOS:A1996TU46300004) 1996 Ball, J B (MEDLINE:2163268) 1990; 3 Chou (10.1016/j.tet.2004.09.054_bib2) 2000; 286 Hoye (10.1016/j.tet.2004.09.054_bib23) 2004; 6 Ball (10.1016/j.tet.2004.09.054_bib4) 1990; 3 Weiss (10.1016/j.tet.2004.09.054_bib1_1) 1998; 5 Kim (10.1016/j.tet.2004.09.054_bib7_2) 1996; 61 Kaval (10.1016/j.tet.2004.09.054_bib15_10) 2003; 7 Hanessian (10.1016/j.tet.2004.09.054_bib3_2) 1997; 53 Van der Eycken (10.1016/j.tet.2004.09.054_bib19) 2002; 67 Azzam (10.1016/j.tet.2004.09.054_bib15_1) 2004; 45 Ball (10.1016/j.tet.2004.09.054_bib11) 1993; 49 Mohamadi (10.1016/j.tet.2004.09.054_bib10) 1990; 11 De Borggraeve (10.1016/j.tet.2004.09.054_bib14) 2001; 42 Hruby (10.1016/j.tet.2004.09.054_bib3_1) 2000; 7 10.1016/j.tet.2004.09.054_bib12 Rombouts (10.1016/j.tet.2004.09.054_bib9_1) 2003 Takeuchi (10.1016/j.tet.2004.09.054_bib9_2) 1998; 120 Vekemans (10.1016/j.tet.2004.09.054_bib13) 1983; 20 Dumas (10.1016/j.tet.2004.09.054_bib7_1) 1994; 35 Rombouts (10.1016/j.tet.2004.09.054_bib15_3) 2001; 42 Liskamp (10.1016/j.tet.2004.09.054_bib3_3) 1994; 113 Buysens (10.1016/j.tet.2004.09.054_bib15_8) 1996 Pataï (10.1016/j.tet.2004.09.054_bib22) 1970 Kemp (10.1016/j.tet.2004.09.054_bib6_1) 1982; 23 Nagai (10.1016/j.tet.2004.09.054_bib5) 1993; 49 Kemp (10.1016/j.tet.2004.09.054_bib6_3) 1982; 23 Kemp (10.1016/j.tet.2004.09.054_bib6_2) 1984; 49 De Borggraeve (10.1016/j.tet.2004.09.054_bib15_2) 2002; 43 Govaerts (10.1016/j.tet.2004.09.054_bib15_5) 2003; 59 Jabs (10.1016/j.tet.2004.09.054_bib1_2) 1999; 286 Kaval (10.1016/j.tet.2004.09.054_bib15_9) 2003; 5 Gramberg (10.1016/j.tet.2004.09.054_bib8) 1994; 35 Buysens (10.1016/j.tet.2004.09.054_bib15_7) 1995; 51 Rogiers (10.1016/j.tet.2004.09.054_bib21) 2003; 59 Rombouts (10.1016/j.tet.2004.09.054_bib15_4) 2003; 59 Tahri (10.1016/j.tet.2004.09.054_bib15_6) 1998; 54 Verbist (10.1016/j.tet.2004.09.054_bib20) 2004; 45 |
References_xml | – ident: bib17 – volume: 5 start-page: 676 year: 1998 end-page: 304 ident: bib1 publication-title: Nat. Struct. Biol. contributor: fullname: Hilgenfeld – volume: 20 start-page: 919 year: 1983 end-page: 923 ident: bib13 publication-title: J. Heterocycl. Chem. contributor: fullname: Hoornaert – volume: 35 start-page: 1493 year: 1994 end-page: 1496 ident: bib7 publication-title: Tetrahedron Lett. contributor: fullname: Germanas – volume: 35 start-page: 861 year: 1994 end-page: 864 ident: bib8 publication-title: Tetrahedron Lett. contributor: fullname: Robinson – volume: 49 start-page: 3577 year: 1993 end-page: 3592 ident: bib5 publication-title: Tetrahedron contributor: fullname: Kato – ident: bib24 – volume: 120 start-page: 1868 year: 2003 end-page: 1878 ident: bib9 publication-title: Eur. J. Org. Chem. contributor: fullname: Marshall – volume: 11 start-page: 440 year: 1990 end-page: 467 ident: bib10 publication-title: J. Comput. Chem. contributor: fullname: Still – volume: 59 start-page: 5047 year: 2003 end-page: 5054 ident: bib21 publication-title: Tetrahedron contributor: fullname: Hoornaert – volume: 45 start-page: 4371 year: 2004 end-page: 4374 ident: bib20 publication-title: Tetrahedron Lett. contributor: fullname: Hoornaert – volume: 7 start-page: 945 year: 2000 end-page: 970 ident: bib3 publication-title: Curr. Med. Chem. contributor: fullname: Liskamp – volume: 45 start-page: 1885 year: 2004 end-page: 1888 ident: bib15 publication-title: Tetrahedron Lett. contributor: fullname: Van der Eycken – ident: bib16 – ident: bib18 – volume: 49 start-page: 3467 year: 1993 end-page: 3478 ident: bib11 publication-title: Tetrahedron contributor: fullname: Andrews – volume: 67 start-page: 7904 year: 2002 end-page: 7907 ident: bib19 publication-title: J. Org. Chem. contributor: fullname: Kappe – volume: 6 start-page: 953 year: 2004 end-page: 956 ident: bib23 publication-title: J. Org. Lett. contributor: fullname: Yao – year: 1970 ident: bib22 article-title: The Chemistry of Amides contributor: fullname: Pataï – volume: 3 start-page: 55 year: 1990 end-page: 64 ident: bib4 publication-title: J. Mol. Recognit. contributor: fullname: Alewood – ident: bib25 – volume: 42 start-page: 5693 year: 2001 end-page: 5695 ident: bib14 publication-title: Tetrahedron Lett. contributor: fullname: Hoornaert – volume: 286 start-page: 1 year: 2000 end-page: 16 ident: bib2 publication-title: Anal. Biochem. contributor: fullname: Chou – volume: 23 start-page: 3761 year: 1982 end-page: 3764 ident: bib6 publication-title: Tetrahedron Lett. contributor: fullname: Sun – volume: 5 start-page: 676 year: 1998 ident: WOS:000075044600009 article-title: Peptide bonds revisited publication-title: NATURE STRUCTURAL BIOLOGY contributor: fullname: Weiss, MS – volume: 67 start-page: 7904 year: 2002 ident: WOS:000178820200052 article-title: High-speed microwave-promoted hetero-Diels-Alder reactions of 2(1H)-pyrazinones in ionic liquid doped solvents publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo0263216 contributor: fullname: Van der Eycken, E – volume: 49 start-page: 3577 year: 1993 ident: WOS:A1993LA10200013 article-title: BICYCLIC TURNED DIPEPTIDE (BTD) AS A BETA-TURN MIMETIC - ITS DESIGN, SYNTHESIS AND INCORPORATION INTO BIOACTIVE PEPTIDES publication-title: TETRAHEDRON contributor: fullname: NAGAI, U – volume: 11 start-page: 440 year: 1990 ident: WOS:A1990CZ22100004 article-title: MACROMODEL - AN INTEGRATED SOFTWARE SYSTEM FOR MODELING ORGANIC AND BIOORGANIC MOLECULES USING MOLECULAR MECHANICS publication-title: JOURNAL OF COMPUTATIONAL CHEMISTRY contributor: fullname: MOHAMADI, F – volume: 61 start-page: 3138 year: 1996 ident: WOS:A1996UJ09400037 article-title: Novel bicyclic lactams as XaaPro type VI beta turn mimics: Design, synthesis, and evaluation publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: Kim, KH – volume: 35 start-page: 861 year: 1994 ident: WOS:A1994MV16900014 article-title: DESIGN AND SYNTHESIS OF A CIS-GLY-PRO, TYPE-VI TURN, DIPEPTIDE MIMETIC AND ITS USE IN FMOC-SOLID PHASE PEPTIDE-SYNTHESIS publication-title: TETRAHEDRON LETTERS contributor: fullname: GRAMBERG, D – volume: 7 start-page: 125 year: 2003 ident: WOS:000207200600005 article-title: Microwave-enhanced transition metal-catalyzed decoration of 2(1H)-pyrazinone scaffolds publication-title: MOLECULAR DIVERSITY contributor: fullname: Kaval, N – volume: 5 start-page: 560 year: 2003 ident: WOS:000185247200003 article-title: An exploratory study on microwave-assisted solid-phase Diels-Alder reactions of 2(1H)-pyrazinones: the elaboration of a new tailor-made acid-labile linker publication-title: JOURNAL OF COMBINATORIAL CHEMISTRY doi: 10.1021/cc0300098 contributor: fullname: Kaval, N – volume: 43 start-page: 447 year: 2002 ident: WOS:000173262000026 article-title: Stereoselective intramolecular Diels-Alder reactions of 3-alkenyl(oxy)-2(1H)-pyrazinones publication-title: TETRAHEDRON LETTERS contributor: fullname: De Borggraeve, WM – volume: 49 start-page: 2286 year: 1984 ident: WOS:A1984SW65900042 article-title: AN EFFICIENT SYNTHESIS OF ETHYL LL-3-AMINO-2-PIPERIDONE-6-CARBOXYLATE publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: KEMP, DS – volume: 286 start-page: 1 year: 2000 ident: WOS:000165201200001 article-title: Prediction of tight turns and their types in proteins publication-title: ANALYTICAL BIOCHEMISTRY doi: 10.1006/abio.2000.4757 contributor: fullname: Chou, KC – volume: 54 start-page: 13211 year: 1998 ident: WOS:000076290600019 article-title: Synthesis of alpha-carbolines and beta-carbolinones via intramolecular Diels-Alder reactions of 2(1H)-pyrazinones publication-title: TETRAHEDRON contributor: fullname: Tahri, A – volume: 286 start-page: 291 year: 1999 ident: WOS:000078702000023 article-title: Non-proline cis peptide bonds in proteins publication-title: JOURNAL OF MOLECULAR BIOLOGY contributor: fullname: Jabs, A – volume: 59 start-page: 5481 year: 2003 ident: WOS:000184164900013 article-title: Diels-Alder reactions of pyridinone o-quinodimethanes generated from substituted sulfolene[3,4-c]pyridin-4(1H)-ones publication-title: TETRAHEDRON doi: 10.1016/S0040-4020(03)00826-3 contributor: fullname: Govaerts, TC – start-page: 824 year: 1970 ident: WOS:000225148000031.25 publication-title: CHEM AMIDES contributor: fullname: PATAI S – volume: 45 start-page: 4371 year: 2004 ident: WOS:000221564200039 article-title: Acid catalysed methanolysis of 2,5-diazabicyclo[2.2.2]octane-3,6-diones: scope and limitations publication-title: TETRAHEDRON LETTERS doi: 10.1016/j.tetlet.2004.03.186 contributor: fullname: Verbist, BMP – volume: 45 start-page: 1885 year: 2004 ident: WOS:000189116200016 article-title: New routes for the synthesis of 3-and 5-substituted 2(1H)-pyrazinones publication-title: TETRAHEDRON LETTERS doi: 10.1016/j.tetlet.2004.01.017 contributor: fullname: Azzam, R – volume: 113 start-page: 1 year: 1994 ident: WOS:A1994NC25600001 article-title: CONFORMATIONALLY RESTRICTED AMINO-ACIDS AND DIPEPTIDES, (NON)PEPTIDOMIMETICS AND SECONDARY STRUCTURE MIMETICS publication-title: RECUEIL DES TRAVAUX CHIMIQUES DES PAYS-BAS-JOURNAL OF THE ROYAL NETHERLANDS CHEMICAL SOCIETY contributor: fullname: LISKAMP, RMJ – volume: 20 start-page: 919 year: 1983 ident: WOS:A1983RE04100014 article-title: A NEW SYNTHESIS OF SUBSTITUTED 2(1H)-PYRAZINONES publication-title: JOURNAL OF HETEROCYCLIC CHEMISTRY contributor: fullname: VEKEMANS, J – volume: 53 start-page: 12789 year: 1997 ident: WOS:A1997XW84000002 article-title: Design and synthesis of conformationally constrained amino acids as versatile scaffolds and peptide mimetics publication-title: TETRAHEDRON contributor: fullname: Hanessian, S – volume: 6 start-page: 953 year: 2004 ident: WOS:000225148000031.13 publication-title: J ORG LETT contributor: fullname: HOYE TR – volume: 35 start-page: 1493 year: 1994 ident: WOS:A1994MZ86100007 article-title: DESIGN, SYNTHESIS AND EVALUATION OF A NOVEL BICYCLIC LACTAM AS A GLY-PRO TYPE-VI BETA-TURN MIMIC publication-title: TETRAHEDRON LETTERS contributor: fullname: DUMAS, JP – volume: 51 start-page: 12463 year: 1995 ident: WOS:A1995TD21800027 article-title: INTRAMOLECULAR DIELS-ALDER REACTIONS OF 2(1H)-PYRAZINONES - SYNTHESIS OF NEW FURO/PYRANO-PYRIDINONES AND FURO/PYRANO-PYRIDINES publication-title: TETRAHEDRON contributor: fullname: BUYSENS, KJ – volume: 42 start-page: 7397 year: 2001 ident: WOS:000171456400017 article-title: Intramolecular Diels-Alder reactions of N-alkenyl-2(1H)-pyrazinones: generation of a novel type of cis-1,7-naphthyridine publication-title: TETRAHEDRON LETTERS contributor: fullname: Rombouts, FJR – volume: 3 start-page: 55 year: 1990 ident: MEDLINE:2163268 article-title: Conformational constraints: nonpeptide beta-turn mimics. publication-title: Journal of molecular recognition : JMR contributor: fullname: Ball, J B – volume: 42 start-page: 5693 year: 2001 ident: WOS:000170309700025 article-title: Synthesis of a conformationally restricted dipeptide analogue and its evaluation as a beta-turn mimic publication-title: TETRAHEDRON LETTERS contributor: fullname: De Borggraeve, WM – volume: 23 start-page: 3759 year: 1982 ident: WOS:A1982PE98500006 article-title: AMINO-ACID DERIVATIVES THAT STABILIZE SECONDARY STRUCTURES OF POLYPEPTIDES .1. SYNTHESIS OF LL-3-AMINO-2-PIPERIDONE-6-CARBOXYLIC ACID (LL-ACP), A NOVEL BETA-TURN-FORMING AMINO-ACID publication-title: TETRAHEDRON LETTERS contributor: fullname: KEMP, DS – start-page: 231 year: 1996 ident: WOS:A1996TU46300004 article-title: Generation of 6-alkylidene/benzylidene-3,6-dihydropyrazin-2(1H)-ones by reaction of 6-bromomethylpyrazin-2(1H)-ones with methoxide and further conversion into specific piperazine-2,5-diones and pyrazin-2(1H)-ones publication-title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 contributor: fullname: Buysens, KJ – volume: 2003 start-page: 1868 year: 2003 ident: WOS:000183105000007 article-title: Development of a functionalizable external beta-turn mimic based on a cis-fused 1,7-naphthyridine scaffold publication-title: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY doi: 10.1002/ejoc.200200652 contributor: fullname: Rombouts, FJR – volume: 59 start-page: 5047 year: 2003 ident: WOS:000183860800016 article-title: Stereoselective transformation of pyrazinones into substituted analogues of cis-5-amino-6-oxo-2-piperidinemethanol and cis-5-amino-2-piperidinemethanol publication-title: TETRAHEDRON doi: 10.1016/S0040-4020(03)00741-5 contributor: fullname: Rogiers, J – volume: 23 start-page: 3761 year: 1982 ident: WOS:A1982PE98500007 article-title: AMINO-ACID DERIVATIVES THAT STABILIZE SECONDARY STRUCTURES OF POLYPEPTIDES .2. THE MOST STABLE CONFORMATION OF PEPTIDES CONTAINING 3-AMINO-2-PIPERIDONE-6-CARBOXYLIC ACID (ACP) publication-title: TETRAHEDRON LETTERS contributor: fullname: KEMP, DS – volume: 120 start-page: 5363 year: 1998 ident: WOS:000074213800002 article-title: Conformational analysis of reverse-turn constraints by N-methylation and N-hydroxylation of amide bonds in peptides and non-peptide mimetics publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: Takeuchi, Y – volume: 59 start-page: 4721 year: 2003 ident: WOS:000183780900002 article-title: Synthesis and conformational analysis of Substance P antagonist analogues based on a 1,7-naphthyridine scaffold publication-title: TETRAHEDRON doi: 10.1016/S0040-4020(03)00732-4 contributor: fullname: Rombouts, FJR – volume: 49 start-page: 3467 year: 1993 ident: WOS:A1993LA10200004 article-title: BETA-TURN TOPOGRAPHY publication-title: TETRAHEDRON contributor: fullname: BALL, JB – volume: 7 start-page: 945 year: 2000 ident: WOS:000088981000006 article-title: Conformational and topographical considerations in designing agonist peptidomimetics from peptide leads publication-title: CURRENT MEDICINAL CHEMISTRY contributor: fullname: Hruby, VJ – volume: 23 start-page: 3761 year: 1982 ident: 10.1016/j.tet.2004.09.054_bib6_1 publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(00)87700-X contributor: fullname: Kemp – volume: 286 start-page: 291 year: 1999 ident: 10.1016/j.tet.2004.09.054_bib1_2 publication-title: J. Mol. Biol. doi: 10.1006/jmbi.1998.2459 contributor: fullname: Jabs – volume: 49 start-page: 2286 year: 1984 ident: 10.1016/j.tet.2004.09.054_bib6_2 publication-title: J. Org. Chem. doi: 10.1021/jo00186a042 contributor: fullname: Kemp – volume: 59 start-page: 5047 year: 2003 ident: 10.1016/j.tet.2004.09.054_bib21 publication-title: Tetrahedron doi: 10.1016/S0040-4020(03)00741-5 contributor: fullname: Rogiers – volume: 113 start-page: 1 year: 1994 ident: 10.1016/j.tet.2004.09.054_bib3_3 publication-title: Recl. Trav. Chim. Pays-Bas. doi: 10.1002/recl.19941130102 contributor: fullname: Liskamp – volume: 42 start-page: 5693 year: 2001 ident: 10.1016/j.tet.2004.09.054_bib14 publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(01)01080-2 contributor: fullname: De Borggraeve – year: 1970 ident: 10.1016/j.tet.2004.09.054_bib22 contributor: fullname: Pataï – volume: 7 start-page: 945 year: 2000 ident: 10.1016/j.tet.2004.09.054_bib3_1 publication-title: Curr. Med. Chem. doi: 10.2174/0929867003374499 contributor: fullname: Hruby – volume: 5 start-page: 676 year: 1998 ident: 10.1016/j.tet.2004.09.054_bib1_1 publication-title: Nat. Struct. Biol. doi: 10.1038/1368 contributor: fullname: Weiss – volume: 43 start-page: 447 year: 2002 ident: 10.1016/j.tet.2004.09.054_bib15_2 publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(01)02188-8 contributor: fullname: De Borggraeve – volume: 7 start-page: 125 year: 2003 ident: 10.1016/j.tet.2004.09.054_bib15_10 publication-title: Mol. Divers. doi: 10.1023/B:MODI.0000006807.43408.d5 contributor: fullname: Kaval – volume: 54 start-page: 13211 year: 1998 ident: 10.1016/j.tet.2004.09.054_bib15_6 publication-title: Tetrahedron doi: 10.1016/S0040-4020(98)00802-3 contributor: fullname: Tahri – volume: 6 start-page: 953 year: 2004 ident: 10.1016/j.tet.2004.09.054_bib23 publication-title: J. Org. Lett. doi: 10.1021/ol049979+ contributor: fullname: Hoye – volume: 286 start-page: 1 year: 2000 ident: 10.1016/j.tet.2004.09.054_bib2 publication-title: Anal. Biochem. doi: 10.1006/abio.2000.4757 contributor: fullname: Chou – volume: 5 start-page: 560 year: 2003 ident: 10.1016/j.tet.2004.09.054_bib15_9 publication-title: J. Comb. Chem. doi: 10.1021/cc0300098 contributor: fullname: Kaval – volume: 35 start-page: 1493 year: 1994 ident: 10.1016/j.tet.2004.09.054_bib7_1 publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(00)76740-2 contributor: fullname: Dumas – volume: 11 start-page: 440 year: 1990 ident: 10.1016/j.tet.2004.09.054_bib10 publication-title: J. Comput. Chem. doi: 10.1002/jcc.540110405 contributor: fullname: Mohamadi – volume: 23 start-page: 3759 year: 1982 ident: 10.1016/j.tet.2004.09.054_bib6_3 publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(00)87699-6 contributor: fullname: Kemp – volume: 61 start-page: 3138 year: 1996 ident: 10.1016/j.tet.2004.09.054_bib7_2 publication-title: J. Org. Chem. doi: 10.1021/jo960012w contributor: fullname: Kim – volume: 59 start-page: 4721 year: 2003 ident: 10.1016/j.tet.2004.09.054_bib15_4 publication-title: Tetrahedron doi: 10.1016/S0040-4020(03)00732-4 contributor: fullname: Rombouts – volume: 20 start-page: 919 year: 1983 ident: 10.1016/j.tet.2004.09.054_bib13 publication-title: J. Heterocycl. Chem. doi: 10.1002/jhet.5570200414 contributor: fullname: Vekemans – volume: 51 start-page: 12463 year: 1995 ident: 10.1016/j.tet.2004.09.054_bib15_7 publication-title: Tetrahedron doi: 10.1016/0040-4020(95)00802-F contributor: fullname: Buysens – volume: 45 start-page: 4371 year: 2004 ident: 10.1016/j.tet.2004.09.054_bib20 publication-title: Tetrahedron Lett. doi: 10.1016/j.tetlet.2004.03.186 contributor: fullname: Verbist – volume: 45 start-page: 1885 year: 2004 ident: 10.1016/j.tet.2004.09.054_bib15_1 publication-title: Tetrahedron Lett. doi: 10.1016/j.tetlet.2004.01.017 contributor: fullname: Azzam – start-page: 1868 year: 2003 ident: 10.1016/j.tet.2004.09.054_bib9_1 publication-title: Eur. J. Org. Chem. doi: 10.1002/ejoc.200200652 contributor: fullname: Rombouts – volume: 67 start-page: 7904 year: 2002 ident: 10.1016/j.tet.2004.09.054_bib19 publication-title: J. Org. Chem. doi: 10.1021/jo0263216 contributor: fullname: Van der Eycken – volume: 53 start-page: 12789 year: 1997 ident: 10.1016/j.tet.2004.09.054_bib3_2 publication-title: Tetrahedron doi: 10.1016/S0040-4020(97)00298-6 contributor: fullname: Hanessian – volume: 49 start-page: 3577 year: 1993 ident: 10.1016/j.tet.2004.09.054_bib5 publication-title: Tetrahedron doi: 10.1016/S0040-4020(01)90216-9 contributor: fullname: Nagai – volume: 59 start-page: 5481 year: 2003 ident: 10.1016/j.tet.2004.09.054_bib15_5 publication-title: Tetrahedron doi: 10.1016/S0040-4020(03)00826-3 contributor: fullname: Govaerts – volume: 35 start-page: 861 year: 1994 ident: 10.1016/j.tet.2004.09.054_bib8 publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(00)75983-1 contributor: fullname: Gramberg – volume: 120 start-page: 5363 year: 1998 ident: 10.1016/j.tet.2004.09.054_bib9_2 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja970855k contributor: fullname: Takeuchi – volume: 49 start-page: 3467 year: 1993 ident: 10.1016/j.tet.2004.09.054_bib11 publication-title: Tetrahedron doi: 10.1016/S0040-4020(01)90207-8 contributor: fullname: Ball – volume: 42 start-page: 7397 year: 2001 ident: 10.1016/j.tet.2004.09.054_bib15_3 publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(01)01545-3 contributor: fullname: Rombouts – ident: 10.1016/j.tet.2004.09.054_bib12 – volume: 3 start-page: 55 year: 1990 ident: 10.1016/j.tet.2004.09.054_bib4 publication-title: J. Mol. Recognit. doi: 10.1002/jmr.300030202 contributor: fullname: Ball – start-page: 231 year: 1996 ident: 10.1016/j.tet.2004.09.054_bib15_8 publication-title: J. Chem. Soc., Perkin Trans. 1 doi: 10.1039/p19960000231 contributor: fullname: Buysens |
SSID | ssj0001123 |
Score | 1.9315492 |
Snippet | In this paper, a synthetic approach for functionalised 5-aminopiperidinone-2-carboxylate (APC) systems as non-pro
cis-peptide bond containing external β-turn... In this paper, a synthetic approach for functionalised 5-aminopiperidinone-2-carboxylate (APC) systems as non-pro cis-peptide bond containing external... |
Source | Web of Science |
SourceID | crossref webofscience elsevier |
SourceType | Aggregation Database Enrichment Source Index Database Publisher |
StartPage | 11597 |
SubjectTerms | Chemistry Chemistry, Organic Diels–Alder reaction Physical Sciences Pyrazinone Science & Technology Turn mimics |
Title | Design and synthesis of novel type VI-like β-turn mimetics. Diversity at the i+1 and the i+2 position |
URI | https://dx.doi.org/10.1016/j.tet.2004.09.054 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000225148000031 |
Volume | 60 |
WOS | 000225148000031 |
WOSCitedRecordID | wos000225148000031 |
hasFullText | 1 |
inHoldings | 1 |
isFullTextHit | |
isPrint | |
link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV3JTsMwEB215QAXxCrKJh84gdw2jp00R9SCCghOgHqLHMeWwpIiGpC48FF8CN_EOIkrkAAhLlEUxclkHM97Tp5nAPb81Isw9AqqcThQblJGJeOGagR3W3FVJeVE8fwiGF3x07EYN2Dg1sJYWWUd-6uYXkbr-ki39mb3IcvsGl_es7Mf3HgiDMMmzCEccd6CucOTs9HFLCAjpZiJ52wD93OzlHkVulRUVtlOBf8Jnr5BpRKBjpdgsaaO5LCybhkaOl-B-YGr2LYKZljKMYjMUzJ9yZHaTbMpmRiST571HbFfW8n1Cb3LbjV5f6MINjm5z-7tMsZphwydQoPIgmBbkh145aWqfUacvmsNro6PLgcjWtdRoIpFoqA8MKERvhFaK3zEiOMY1r4WKoyMlixSYZD4LOE9pZVMAhmqVDCTSE_2fZUiYVuHVj7J9QYQdLPEbmR9HRhuOJOBREKApAJ5RMoD1oZ95774oUqXETsd2U2MvrZlL3nci2I0pA3cOTj-0ucxhvPfmu197ozZfcpcPsj_-haDfa8N3l9OG9Sp0G0KgGLzfxZtwYLL_9gLtqFVPD7pHeQqRbILzc6rt1u_kR9FOua9 |
link.rule.ids | 315,786,790,4521,24144,27957,27958,45620,45714 |
linkProvider | Elsevier |
linkToHtml | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV1LT8MwDLZgHOCCeIrxzIETKLCmSbsepw208dgJELcqTROpMDrEChJ_ix_Cb8JpmwkkQIhLVVVN69qN_aX9bAPs-6kXoesVVON0oNykjErGDdUY3G3HVZWUC8XLYdC_5me34nYGui4XxtIqa99f-fTSW9dHjmttHj9mmc3x5S27-sGNJ8IwnIU5LkKPN2CuMzjvD6cOGSHFlDxnB7ifmyXNq9Alo7Kqdir4T-Hpm6hURqDTJVisoSPpVNItw4zOV2C-6zq2rYLplXQMIvOUTF5zhHaTbELGhuTjFz0i9msruRnQUXavyfsbxWCTk4fswaYxTo5IzzE0iCwIjiXZoVdeqtpnxPG71uD69OSq26d1HwWqWCQKygMTGuEbobXCR4w4zmHta6HCyGjJIhUGic8S3lJaySSQoUoFM4n0ZNtXKQK2dWjk41xvAEE1SzQja-vAcMOZDCQCAgQViCNSHrAmHDj1xY9VuYzY8cjuYtS1bXvJ41YUoyBN4E7B8Rebx-jOfxu2_9kY0_uUtXwQ_7VtDPa9Jnh_Oa1bl0K3JQCKzf9JtAfz_avLi_hiMDzfggVXC7IVbEOjeHrWO4hbimS3fi8_ANas6K8 |
openUrl | ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Design+and+synthesis+of+novel+type+VI-like+%CE%B2-turn+mimetics.+Diversity+at+the+i%2B1+and+the+i%2B2+position&rft.jtitle=Tetrahedron&rft.au=De+Borggraeve%2C+Wim+M.&rft.au=Verbist%2C+Bie+M.P.&rft.au=Rombouts%2C+Frederik+J.R.&rft.au=Pawar%2C+Vijaykumar+G.&rft.date=2004-12-06&rft.pub=Elsevier+Ltd&rft.issn=0040-4020&rft.eissn=1464-5416&rft.volume=60&rft.issue=50&rft.spage=11597&rft.epage=11612&rft_id=info:doi/10.1016%2Fj.tet.2004.09.054&rft.externalDocID=S0040402004015777 |
thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0040-4020&client=summon |
thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0040-4020&client=summon |
thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0040-4020&client=summon |