A Thioethylalkylamido (TEA) Thioester Surrogate in the Synthesis of a Cyclic Peptide via a Tandem Acyl Shift

The cyclic cystine-knot peptide, kalata B1, was synthesized by employing a novel Fmoc-compatible thioethylalkylamido (TEA) thioester surrogate via an N–S acyl shift followed by a thiol-thioester exchange reaction. TEA thioester surrogate is cost-effective, conveniently prepared in one-step with star...

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Bibliographic Details
Published inOrganic letters Vol. 15; no. 11; pp. 2620 - 2623
Main Authors Taichi, Misako, Hemu, Xinya, Qiu, Yibo, Tam, James P
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.06.2013
Amer Chemical Soc
Subjects
Amides - chemical synthesis
Amides - chemistry
Chemistry
Chemistry, Organic
Cyclotides - chemical synthesis
Cyclotides - chemistry
Peptides - chemistry
Peptides, Cyclic - chemical synthesis
Peptides, Cyclic - chemistry
Physical Sciences
Science & Technology
Sulfhydryl Compounds - chemical synthesis
Sulfhydryl Compounds - chemistry
ASSISTED THIOESTERIFICATION
SEGMENT
SOLID-PHASE SYNTHESIS
NATIVE CHEMICAL LIGATION
POLYPEPTIDE
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Summary:The cyclic cystine-knot peptide, kalata B1, was synthesized by employing a novel Fmoc-compatible thioethylalkylamido (TEA) thioester surrogate via an N–S acyl shift followed by a thiol-thioester exchange reaction. TEA thioester surrogate is cost-effective, conveniently prepared in one-step with starting materials, readily available from commercial sources, and highly efficient in preparing peptide thioesters.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol400801k