rdf:type |
|
lifeskim:mentions |
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pubmed:issue |
11
|
pubmed:dateCreated |
2008-10-27
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pubmed:abstractText |
A novel strategy for a more efficient synthesis of difficult sequence-containing peptides, the S-acyl isopeptide method, was developed and successfully applied. A model pentapeptide Ac-Val-Val-Cys-Val-Val-NH2 was synthesized via its water-soluble S-acyl isopeptide using an S-acyl isodipeptide unit, Boc-Cys(Fmoc-Val)-OH. An S-acyl isopeptide possessing excellent water solubility could be readily and quantitatively converted to the native peptide via an S--N intramolecular acyl migration reaction at pH 7.4. Thus, the S-acyl isopeptide method provides a useful tool in peptide chemistry.
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pubmed:language |
eng
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pubmed:journal |
|
pubmed:citationSubset |
IM
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pubmed:chemical |
|
pubmed:status |
MEDLINE
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pubmed:month |
Nov
|
pubmed:issn |
1075-2617
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pubmed:author |
|
pubmed:copyrightInfo |
Copyright (c) 2008 European Peptide Society and John Wiley & Sons, Ltd.
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pubmed:issnType |
Print
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pubmed:volume |
14
|
pubmed:owner |
NLM
|
pubmed:authorsComplete |
Y
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pubmed:pagination |
1203-8
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pubmed:meshHeading |
pubmed-meshheading:18613286-Amino Acid Sequence,
pubmed-meshheading:18613286-Carbamates,
pubmed-meshheading:18613286-Chemistry,
pubmed-meshheading:18613286-Chromatography, High Pressure Liquid,
pubmed-meshheading:18613286-Cysteine,
pubmed-meshheading:18613286-Fluorides,
pubmed-meshheading:18613286-Hydrogen-Ion Concentration,
pubmed-meshheading:18613286-Models, Chemical,
pubmed-meshheading:18613286-Molecular Sequence Data,
pubmed-meshheading:18613286-Molecular Structure,
pubmed-meshheading:18613286-Peptide Fragments,
pubmed-meshheading:18613286-Peptides,
pubmed-meshheading:18613286-Solubility
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pubmed:year |
2008
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pubmed:articleTitle |
Isopeptide method: development of S-acyl isopeptide method for the synthesis of difficult sequence-containing peptides.
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pubmed:affiliation |
Department of Medicinal Chemistry, Division of Medicinal Chemical Sciences, Center for Frontier Research in Medicinal Science, 21st Century COE Program, Kyoto Pharmaceutical University, Yamashina-ku, Kyoto, Japan.
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pubmed:publicationType |
Journal Article,
Research Support, Non-U.S. Gov't
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