A thioethylalkylamido (TEA) thioester surrogate in the synthesis of a cyclic peptide via a tandem acyl shift

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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Main Authors: Taichi, Misako, Hemu, Xinya, Qiu, Yibo, Tam, James P.
Other Authors: School of Biological Sciences
Format: Article
Language:English
Published: 2013
Subjects:
DRNTU::Science::Biological sciences::Biochemistry
Online Access:https://hdl.handle.net/10356/107258
http://hdl.handle.net/10220/18147
http://dx.doi.org/10.1021/ol400801k
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-1072582019-12-06T22:27:30Z A thioethylalkylamido (TEA) thioester surrogate in the synthesis of a cyclic peptide via a tandem acyl shift Taichi, Misako Hemu, Xinya Qiu, Yibo Tam, James P. School of Biological Sciences DRNTU::Science::Biological sciences::Biochemistry 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. 2013-12-06T07:23:18Z 2019-12-06T22:27:30Z 2013-12-06T07:23:18Z 2019-12-06T22:27:30Z 2013 2013 Journal Article Taichi, M., Hemu, X., Qiu, Y., & Tam, J. P. (2013). A thioethylalkylamido (TEA) thioester surrogate in the synthesis of a cyclic peptide via a tandem acyl shift. Organic letters, 15(11), 2620-2623. https://hdl.handle.net/10356/107258 http://hdl.handle.net/10220/18147 http://dx.doi.org/10.1021/ol400801k en Organic letters
institution Nanyang Technological University
building NTU Library
country Singapore
collection DR-NTU
language English
topic DRNTU::Science::Biological sciences::Biochemistry
spellingShingle DRNTU::Science::Biological sciences::Biochemistry
Taichi, Misako
Hemu, Xinya
Qiu, Yibo
Tam, James P.
A thioethylalkylamido (TEA) thioester surrogate in the synthesis of a cyclic peptide via a tandem acyl shift
description 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.
author2 School of Biological Sciences
author_facet School of Biological Sciences
Taichi, Misako
Hemu, Xinya
Qiu, Yibo
Tam, James P.
format Article
author Taichi, Misako
Hemu, Xinya
Qiu, Yibo
Tam, James P.
author_sort Taichi, Misako
title A thioethylalkylamido (TEA) thioester surrogate in the synthesis of a cyclic peptide via a tandem acyl shift
title_short A thioethylalkylamido (TEA) thioester surrogate in the synthesis of a cyclic peptide via a tandem acyl shift
title_full A thioethylalkylamido (TEA) thioester surrogate in the synthesis of a cyclic peptide via a tandem acyl shift
title_fullStr A thioethylalkylamido (TEA) thioester surrogate in the synthesis of a cyclic peptide via a tandem acyl shift
title_full_unstemmed A thioethylalkylamido (TEA) thioester surrogate in the synthesis of a cyclic peptide via a tandem acyl shift
title_sort thioethylalkylamido (tea) thioester surrogate in the synthesis of a cyclic peptide via a tandem acyl shift
publishDate 2013
url https://hdl.handle.net/10356/107258
http://hdl.handle.net/10220/18147
http://dx.doi.org/10.1021/ol400801k
_version_ 1681045486318911488

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