A Simple Method for Deprotection of the N- and O-Carbobenzoxy Groups and N-Methylation of the Desosamine Sugar Moiety of Ketolides
A simple synthetic method for deprotection of the N- and O-carbobenzoxy groups (Cbz) of the desosamine sugar moiety of ketolides is reported. This deprotection method is applicable to the synthesis of a variety of ketolide analogues with various 9-iminoether moieties in good to moderate yield. Among...
Saved in:
Published in | Journal of antibiotics Vol. 58; no. 11; p. 679 |
---|---|
Main Authors | , , , |
Format | Journal Article |
Language | English |
Published |
Tokyo
Nature Publishing Group
01.11.2005
|
Subjects | |
Online Access | Get full text |
Cover
Loading…
Abstract | A simple synthetic method for deprotection of the N- and O-carbobenzoxy groups (Cbz) of the desosamine sugar moiety of ketolides is reported. This deprotection method is applicable to the synthesis of a variety of ketolide analogues with various 9-iminoether moieties in good to moderate yield. Among the ketolide derivatives prepared by this method, compound 7g with a quinoline-6-yl moiety showed potent activity against erythromycin-resistant pathogens as well as Haemophilus influenzae. |
---|---|
AbstractList | A simple synthetic method for deprotection of the N- and O-carbobenzoxy groups (Cbz) of the desosamine sugar moiety of ketolides is reported. This deprotection method is applicable to the synthesis of a variety of ketolide analogues with various 9-iminoether moieties in good to moderate yield. Among the ketolide derivatives prepared by this method, compound 7g with a quinoline-6-yl moiety showed potent activity against erythromycin-resistant pathogens as well as Haemophilus influenzae. |
Author | Iwaki, Tsutomu Narukawa, Yukitoshi Nomura, Takashi Uotani, Koichi |
Author_xml | – sequence: 1 givenname: Tsutomu surname: Iwaki fullname: Iwaki, Tsutomu – sequence: 2 givenname: Takashi surname: Nomura fullname: Nomura, Takashi – sequence: 3 givenname: Yukitoshi surname: Narukawa fullname: Narukawa, Yukitoshi – sequence: 4 givenname: Koichi surname: Uotani fullname: Uotani, Koichi |
BookMark | eNpNkE1PAjEYhBuDiYBe_AVNPBf7sdD2SEDRyMcBPZN2-1aWLC1udxPw6C93UQ-e5jCZZzLTQ50QAyB0y-iAUaHud2bAKR0OtLhAXaYUIywb6Q7qUsoZUYrTK9RLaUepkEKqLvoa43WxP5SAF1Bvo8M-VngKhyrWkNdFDDh6XG8BLwk2weEVmZjKRgvhMx5PeFbF5pB-nCU5E06l-Z-aQorJ7IsAeN28mwovYgH16Wy_QB3LwkG6RpfelAlu_rSP3h4fXidPZL6aPU_Gc5IzOhREMW5yYbVhUmUqs96InHPHuVHgMuUZ6KGXQjvKuLQjx72jVnglgCkN1og-uvvltuM-Gkj1ZhebKrSVmxYp228k1eIbaJRi4Q |
CitedBy_id | crossref_primary_10_1002_chin_200618193 crossref_primary_10_1016_j_bmc_2006_01_036 crossref_primary_10_1111_bph_13936 |
ContentType | Journal Article |
Copyright | Copyright Nature Publishing Group Nov 2005 |
Copyright_xml | – notice: Copyright Nature Publishing Group Nov 2005 |
DBID | 3V. 7QL 7T5 7X7 7XB 88E 88I 8FE 8FH 8FI 8FJ 8FK ABUWG AFKRA AZQEC BBNVY BENPR BHPHI C1K CCPQU DWQXO FYUFA GHDGH GNUQQ H94 HCIFZ K9. LK8 M0S M1P M2P M7P PQEST PQQKQ PQUKI Q9U |
DOI | 10.1038/ja.2005.93 |
DatabaseName | ProQuest Central (Corporate) Bacteriology Abstracts (Microbiology B) Immunology Abstracts Health & Medical Collection ProQuest Central (purchase pre-March 2016) Medical Database (Alumni Edition) Science Database (Alumni Edition) ProQuest SciTech Collection ProQuest Natural Science Collection Hospital Premium Collection Hospital Premium Collection (Alumni Edition) ProQuest Central (Alumni) (purchase pre-March 2016) ProQuest Central (Alumni) ProQuest Central ProQuest Central Essentials Biological Science Collection ProQuest Central Natural Science Collection Environmental Sciences and Pollution Management ProQuest One Community College ProQuest Central Korea Health Research Premium Collection Health Research Premium Collection (Alumni) ProQuest Central Student AIDS and Cancer Research Abstracts SciTech Premium Collection (Proquest) (PQ_SDU_P3) ProQuest Health & Medical Complete (Alumni) ProQuest Biological Science Collection Health & Medical Collection (Alumni Edition) Medical Database Science Database Biological Science Database ProQuest One Academic Eastern Edition (DO NOT USE) ProQuest One Academic ProQuest One Academic UKI Edition ProQuest Central Basic |
DatabaseTitle | ProQuest Central Student ProQuest Central Essentials ProQuest Health & Medical Complete (Alumni) ProQuest Central (Alumni Edition) SciTech Premium Collection ProQuest One Community College ProQuest Natural Science Collection Environmental Sciences and Pollution Management ProQuest Central Health Research Premium Collection Health and Medicine Complete (Alumni Edition) Natural Science Collection ProQuest Central Korea Bacteriology Abstracts (Microbiology B) Biological Science Collection AIDS and Cancer Research Abstracts ProQuest Medical Library (Alumni) ProQuest Science Journals (Alumni Edition) ProQuest Biological Science Collection ProQuest Central Basic ProQuest Science Journals ProQuest One Academic Eastern Edition ProQuest Hospital Collection Health Research Premium Collection (Alumni) Biological Science Database ProQuest SciTech Collection ProQuest Hospital Collection (Alumni) ProQuest Health & Medical Complete ProQuest Medical Library ProQuest One Academic UKI Edition Immunology Abstracts ProQuest One Academic ProQuest Central (Alumni) |
DatabaseTitleList | ProQuest Central Student |
Database_xml | – sequence: 1 dbid: BENPR name: ProQuest Central url: https://www.proquest.com/central sourceTypes: Aggregation Database |
DeliveryMethod | fulltext_linktorsrc |
Discipline | Pharmacy, Therapeutics, & Pharmacology |
EISSN | 1881-1469 |
ExternalDocumentID | 4050620621 |
GroupedDBID | --- -Q- -~X .55 0R~ 29J 2WC 39C 3O- 3V. 4.4 406 53G 5GY 7QL 7T5 7X7 7XB 88E 88I 8FE 8FH 8FI 8FJ 8FK AANZL AAZLF ABAKF ABAWZ ABJNI ABUWG ABZZP ACAOD ACGFS ACKTT ACRQY ACZOJ ADBBV AEFQL AEJRE AEMSY AENEX AEVLU AEXYK AFBBN AFKRA AFSHS AGAYW AGEZK AGHAI AGQEE AHMBA AHSBF AJRNO ALFFA ALIPV ALMA_UNASSIGNED_HOLDINGS AMYLF AXYYD AZQEC BAWUL BBNVY BENPR BHPHI BKKNO BPHCQ BVXVI C1K CCPQU DIK DNIVK DPUIP DU5 DWQXO EBLON EBS EE. EIOEI EJD F5P FDQFY FERAY FIZPM FSGXE FYUFA GNUQQ H94 HCIFZ HMCUK HZ~ IWAJR JSH JSO JZLTJ K9. LK8 M1P M2P M7P NAO NQJWS O9- OK1 P6G PQEST PQQKQ PQUKI PROAC PSQYO Q9U RJT RNT RNTTT SNX SNYQT SOHCF SRMVM SWTZT TAOOD TBHMF TDRGL TKC TR2 TSG UKHRP UPT W2D X7M YQT ZXP |
ID | FETCH-LOGICAL-c1053-812ac3b9a178484bfa3c22d22a8ed48f1e95f739d0127b6d2fd0b3f83e189eba3 |
IEDL.DBID | BENPR |
ISSN | 0021-8820 |
IngestDate | Thu Oct 10 20:50:08 EDT 2024 |
IsDoiOpenAccess | false |
IsOpenAccess | true |
IsPeerReviewed | true |
IsScholarly | true |
Issue | 11 |
Language | English |
LinkModel | DirectLink |
MergedId | FETCHMERGED-LOGICAL-c1053-812ac3b9a178484bfa3c22d22a8ed48f1e95f739d0127b6d2fd0b3f83e189eba3 |
OpenAccessLink | https://www.nature.com/articles/ja200593.pdf |
PQID | 1787820709 |
PQPubID | 2041950 |
ParticipantIDs | proquest_journals_1787820709 |
PublicationCentury | 2000 |
PublicationDate | 20051101 |
PublicationDateYYYYMMDD | 2005-11-01 |
PublicationDate_xml | – month: 11 year: 2005 text: 20051101 day: 01 |
PublicationDecade | 2000 |
PublicationPlace | Tokyo |
PublicationPlace_xml | – name: Tokyo |
PublicationTitle | Journal of antibiotics |
PublicationYear | 2005 |
Publisher | Nature Publishing Group |
Publisher_xml | – name: Nature Publishing Group |
SSID | ssj0037378 |
Score | 1.7527086 |
Snippet | A simple synthetic method for deprotection of the N- and O-carbobenzoxy groups (Cbz) of the desosamine sugar moiety of ketolides is reported. This deprotection... |
SourceID | proquest |
SourceType | Aggregation Database |
StartPage | 679 |
SubjectTerms | Sugar |
Title | A Simple Method for Deprotection of the N- and O-Carbobenzoxy Groups and N-Methylation of the Desosamine Sugar Moiety of Ketolides |
URI | https://www.proquest.com/docview/1787820709 |
Volume | 58 |
hasFullText | 1 |
inHoldings | 1 |
isFullTextHit | |
isPrint | |
link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwfV07b9swECYae8lSpG2KtEmNG4pMYSORlERNhe3GCFpYNfIAvAWkeAwcNFJqOUDdsb-8pETBQIfOB2q4o-6-e_A7Qj7GjEWYiJKWXHAqRJJThdJQK43SzEhUbU13XqSXt-LrMlmGglsTxip7n9g6alOXvkZ-Hrub5aJVFuWfn35SvzXKd1fDCo09MmSx8G3a4eSiWFz1vphnPPhiFlOHJaOeoJTL84eOdeiTbzn_44bb2DI7IC8DKIRxZ8VX5AVWr8npomOV3p7Bze6RVHMGp7DY8U1v35A_Y7heeZJfmLfroMHhUPiCgYHB6R1qCw7nQUFBVQa-06la61pj9bv-tYW2-tS0koL6L2y78bj-lMtM60Y9OjQK18_3ag3z2s95evE33NQ_VgabQ3I7u7iZXtKwWoGWDlBx6sK6KrnOlVOrkEJbxUvGDGNKohHSxpgnNuO58Z1pnRpmTaS5lRxjmaNW_C0ZVHWFRwRcjhsLa7ixmIo0VnkSqSxFl2eh8dQ178hJr9278H80dztrvv-_-Jjsd2SpvuhxQgab9TN-cDBgo0dkL1tmIzIczyaTYhQs_xegLLYJ |
link.rule.ids | 315,786,790,12083,21416,27955,27956,31752,33777,43343,43838,74100,74657 |
linkProvider | ProQuest |
linkToHtml | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwfV1LT-MwELagHOCCeIrXwhwQJwyJ7STOCVXsovJoQaJIvVV2PEZdLQk0RaIc95evnaRbiQPnURJpxpn55uFvCDkOGQswEhnNuOBUiCilCqWhVhqlmZGoqpputxd3nsTNIBo0BbeyGauc-cTKUZsi8zXy89CdLBetkiC9eH2jfmuU7642KzQWyZLg7mPuPCeD_wkXT3jjiVlIHZIMZvSkXJ7_rjmHznzD-YsTriLL1RpZbSAhtGsbrpMFzDfIyUPNKT09hf78ilR5CifwMGebnm6Sv214HHmKX-hWy6DBoVD4iQ3_gtM6FBYcyoMeBZUbuKeXaqwLjfln8TGFqvZUVpIe9W-Y1sNxs6dcXlqU6sVhUXh8f1Zj6BZ-ytOLb3FS_BkZLLfI09Wv_mWHNosVaObgFKcuqKuM61Q5pQoptFU8Y8wwpiQaIW2IaWQTnhrfl9axYdYEmlvJMZQpasW3SSsvctwh4DLcUFjDjcVYxKFKo0AlMbosC40nrtklBzPtDpu_oxzObbn3vfiILHf63bvh3XXvdp-s1LSpvvxxQFqT8Tv-cIBgog8rq_8DPA21LQ |
linkToPdf | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwfV1LT9wwELYoSKgXBJSqtDzmgDjhbmI7iXNCCFjx2u1KgLS3lR2PEYgmdLNILEd-OXbiZaUeOI-cgyeZ-eaR7yNkL2YswkQUtOCCUyGSnCqUhlpplGZGomp6ur1-enYrLobJMOw_1WGtchYTm0BtqsL3yDuxe7NctsqivGPDWsTgpHv49I96BSk_aQ1yGl_IksuSkZdxyIYfxRfPeIjKLKYOVUYzqlIuOw8t_9BvP3z-LyA3Waa7SlYCPISj1p9rZAHLdbI_aPmlpwdwM_9dqj6AfRjMmaen38jbEVzfe7pf6DXC0OAQKZxg4GJwHoDKgkN80KegSgN_6LEa60pj-Vq9TKHpQ9WNpU_9E6btotzslKtRq1r9dbgUrp_v1Bh6ld_49OZLnFSP9wbrDXLbPb05PqNBZIEWDlpx6hK8KrjOlbtgIYW2iheMGcaURCOkjTFPbMZz42fUOjXMmkhzKznGMket-HeyWFYl_iDgqt1YWMONxVSkscqTSGUpuooLjSex2SRbs9sdhS-lHs39-vNz8y5Zdg4fXZ33L3-Rry2Dqu-EbJHFyfgZtx02mOidxunvYTy5WQ |
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=A+Simple+Method+for+Deprotection+of+the+N-+and+O-Carbobenzoxy+Groups+and+N-Methylation+of+the+Desosamine+Sugar+Moiety+of+Ketolides&rft.jtitle=Journal+of+antibiotics&rft.au=Iwaki%2C+Tsutomu&rft.au=Nomura%2C+Takashi&rft.au=Narukawa%2C+Yukitoshi&rft.au=Uotani%2C+Koichi&rft.date=2005-11-01&rft.pub=Nature+Publishing+Group&rft.issn=0021-8820&rft.eissn=1881-1469&rft.volume=58&rft.issue=11&rft.spage=679&rft_id=info:doi/10.1038%2Fja.2005.93&rft.externalDBID=HAS_PDF_LINK&rft.externalDocID=4050620621 |
thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0021-8820&client=summon |
thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0021-8820&client=summon |
thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0021-8820&client=summon |