Solid Phase Synthesis of Isariin, a Long Chain [beta]-Hydroxy Acid-containing Cyclodepsipeptide, and Its Diastereoisomer

The method of solid phase synthesis was applied to the preparation of isariin (Ia), a β-hydroxydodecanoic acid-containing cyclodepsipeptide metabolite of Isaria cretacea, and its isomer (Ib). The open-chain depsipeptide, H-Val-D-Leu-Ala-Val-DL-Hyd-Gly-OH, was synthesized by coupling successively BOC...

Full description

Saved in:
Bibliographic Details
Published inChemical & pharmaceutical bulletin Vol. 22; no. 9; p. 2136
Main Authors OKADA, KOZO, KUROSAWA, YOTARO, HIRAMOTO, MINORU
Format Journal Article
LanguageEnglish
Published Tokyo Japan Science and Technology Agency 01.09.1974
Online AccessGet full text

Cover

Abstract The method of solid phase synthesis was applied to the preparation of isariin (Ia), a β-hydroxydodecanoic acid-containing cyclodepsipeptide metabolite of Isaria cretacea, and its isomer (Ib). The open-chain depsipeptide, H-Val-D-Leu-Ala-Val-DL-Hyd-Gly-OH, was synthesized by coupling successively BOC-Val-DL-Hyd-OH, alanine, and Z-Val-D-Leu-OH to resin-bound glycine using dicyclohexylcarbodiimide (DCC) or DCC+hydroxysuccinimide (HOSu) as coupling agent. After cleavage from the resin the depsipeptide was cyclized by means of DCC+HOSu. The cyclization product was successfully resolved, after chromatographic purification on Dowex 50×4 and Sephadex LH-20 column, by preparative thin-layer chromatography on silica gel to afford Ia and Ib in moderate yields.
AbstractList The method of solid phase synthesis was applied to the preparation of isariin (Ia), a β-hydroxydodecanoic acid-containing cyclodepsipeptide metabolite of Isaria cretacea, and its isomer (Ib). The open-chain depsipeptide, H-Val-D-Leu-Ala-Val-DL-Hyd-Gly-OH, was synthesized by coupling successively BOC-Val-DL-Hyd-OH, alanine, and Z-Val-D-Leu-OH to resin-bound glycine using dicyclohexylcarbodiimide (DCC) or DCC+hydroxysuccinimide (HOSu) as coupling agent. After cleavage from the resin the depsipeptide was cyclized by means of DCC+HOSu. The cyclization product was successfully resolved, after chromatographic purification on Dowex 50×4 and Sephadex LH-20 column, by preparative thin-layer chromatography on silica gel to afford Ia and Ib in moderate yields.
Author OKADA, KOZO
HIRAMOTO, MINORU
KUROSAWA, YOTARO
Author_xml – sequence: 1
  givenname: KOZO
  surname: OKADA
  fullname: OKADA, KOZO
– sequence: 2
  givenname: YOTARO
  surname: KUROSAWA
  fullname: KUROSAWA, YOTARO
– sequence: 3
  givenname: MINORU
  surname: HIRAMOTO
  fullname: HIRAMOTO, MINORU
BookMark eNqNi8FKw0AQQBepYFr9hwGvLmyyXUOOUpUWPAj1JqWs2amZEnfizhaavzeCH-DpHd57czWLHPFCFaVd1tpVlZ2pwhjT6Mre2ys1FzkaUzlT20Kdt9xTgNfOC8J2jLlDIQE-wEZ8Iop34OGF4yesOk8R3j8w-51ejyHxeYSHloJuOebJ0W80tj0HHIQGHDIFnPYYYJMFHslLxoRMwl-YrtXlwfeCN39cqNvnp7fVWg-Jv08oeX_kU4qT2pdL19SNa0pn_1f9ANusUE4
ContentType Journal Article
Copyright Copyright Japan Science and Technology Agency 1974
Copyright_xml – notice: Copyright Japan Science and Technology Agency 1974
DBID 7TK
7TM
7U9
H94
DatabaseName Neurosciences Abstracts
Nucleic Acids Abstracts
Virology and AIDS Abstracts
AIDS and Cancer Research Abstracts
DatabaseTitle Virology and AIDS Abstracts
Nucleic Acids Abstracts
AIDS and Cancer Research Abstracts
Neurosciences Abstracts
DatabaseTitleList Virology and AIDS Abstracts
DeliveryMethod fulltext_linktorsrc
Discipline Pharmacy, Therapeutics, & Pharmacology
EISSN 1347-5223
ExternalDocumentID 3131764801
GroupedDBID ---
.GJ
2WC
53G
5GY
6J9
7TK
7TM
7U9
ACGFO
ACIWK
ACPRK
ADBBV
AENEX
AFRAH
AI.
ALMA_UNASSIGNED_HOLDINGS
BAWUL
CS3
DIK
DU5
EBS
EJD
F5P
GX1
H94
HH5
JSF
JSH
KQ8
L7B
OK1
P2P
RJT
RZJ
TKC
TR2
VH1
X7J
ZGI
ID FETCH-proquest_journals_14597959153
ISSN 0009-2363
IngestDate Thu Oct 10 14:15:17 EDT 2024
IsPeerReviewed true
IsScholarly true
Issue 9
Language English
LinkModel OpenURL
MergedId FETCHMERGED-proquest_journals_14597959153
PQID 1459795915
PQPubID 1996362
ParticipantIDs proquest_journals_1459795915
PublicationCentury 1900
PublicationDate 19740901
PublicationDateYYYYMMDD 1974-09-01
PublicationDate_xml – month: 09
  year: 1974
  text: 19740901
  day: 01
PublicationDecade 1970
PublicationPlace Tokyo
PublicationPlace_xml – name: Tokyo
PublicationTitle Chemical & pharmaceutical bulletin
PublicationYear 1974
Publisher Japan Science and Technology Agency
Publisher_xml – name: Japan Science and Technology Agency
SSID ssj0025073
Score 2.4503942
Snippet The method of solid phase synthesis was applied to the preparation of isariin (Ia), a β-hydroxydodecanoic acid-containing cyclodepsipeptide metabolite of...
SourceID proquest
SourceType Aggregation Database
StartPage 2136
Title Solid Phase Synthesis of Isariin, a Long Chain [beta]-Hydroxy Acid-containing Cyclodepsipeptide, and Its Diastereoisomer
URI https://www.proquest.com/docview/1459795915
Volume 22
hasFullText 1
inHoldings 1
isFullTextHit
isPrint
link http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV1ba9swFBZpn_YytnVjl24IOvrieNS2fHt005ZkTeMscVi2MYJky8TQ2aFOoe7f2B_ekXxL2lK2vRgjYWNzPr5zjnTOJ4Q-MueIc0Ys1Y5jWyWMMdUhrqFG3KJOaFNTp6J3-GJk9Wfk89ycdzq_N6qWrtfsU3j7YF_J_1gVxsCuokv2HyzbvBQG4B7sC1ewMFz_ysbT7DKJlPESPJEyLVKI5Sp5kUEOKXCpDkCVoThOqLekCdjZPGYc4kXzRO0XkahgUbwwiVRRsF4eFaH0ivAyi_gqT1ai4KVU5ZVFw-scCJIKYQWeJXn2q6rrrWUOauUBgaXVcmulnG1qfIsV3XPvxJMU43_3G8qfTfyp91WOf_MDb9LM9AcT78IPfLl4Oxj5k1m7VqFBptIUY1V-BPx_S1ri09v9A8WTvaZbXO2qulHRHy_p2SA2pM5lh3LN37q-gVN3i4yNB1S2R_7ibDYcLoLTebA9W3p1DSIqS4jq7KAdQxNVoudfmo0pCBjt5nA-8XH3XLiMS4Jn6GmVUGCvRMdz1OHpC3Q4Lg1QdHHQNtjlXXyIx61WebGHbiSEsIQQbiCEsxhXEOpiigWAsAQQ_iHg87MGD74DHnwPPPB4GmGADr4DnZfo4Ow06PXV-r8WFeJzSBMh_XRNF7zkK7SbZil_jXBkhBqnjDo0NAh3Y8ehxDAsK9aOXKIT5w3af-xNbx-ffoeetEDaR7vrq2v-HsLANfsgDfMHgs1p4Q
link.rule.ids 315,783,787
linkProvider Colorado Alliance of Research Libraries
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=Solid+Phase+Synthesis+of+Isariin%2C+a+Long+Chain+%5Bbeta%5D-Hydroxy+Acid-containing+Cyclodepsipeptide%2C+and+Its+Diastereoisomer&rft.jtitle=Chemical+%26+pharmaceutical+bulletin&rft.au=OKADA%2C+KOZO&rft.au=KUROSAWA%2C+YOTARO&rft.au=HIRAMOTO%2C+MINORU&rft.date=1974-09-01&rft.pub=Japan+Science+and+Technology+Agency&rft.issn=0009-2363&rft.eissn=1347-5223&rft.volume=22&rft.issue=9&rft.spage=2136&rft.externalDBID=NO_FULL_TEXT&rft.externalDocID=3131764801
thumbnail_l http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0009-2363&client=summon
thumbnail_m http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0009-2363&client=summon
thumbnail_s http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0009-2363&client=summon