Preparation of peptide thioesters through fmoc-based solid-phase peptide synthesis by using amino thioesters

N. Stuhr-Hansen; T.S. Wilbek; K. Strømgaard

doi:10.1002/ejoc.201300927

Preparation of peptide thioesters through fmoc-based solid-phase peptide synthesis by using amino thioesters

N. Stuhr-Hansen, T.S. Wilbek, K. Strømgaard

8 Citations (Scopus)

Abstract

An effective procedure for the synthesis of peptide alkyl thioesters by 9-fluorenylmethoxycarbonyl (Fmoc) solid-phase peptide synthesis was developed. The free C terminus of a fully protected peptide was coupled in solution with the free amino group of an amino thioester. This furnished the fully protected peptide thioester, which was globally deprotected to afford the desired unprotected peptide thioester. The method is compatible with labile groups such as phosphoryl and glycosyl moieties. The synthesis of peptide alkyl thioesters by 9-fluorenylmethoxycarbonyl (Fmoc) solid-phase peptide synthesis (SPPS) is developed. The free C terminus of a fully protected peptide is coupled in solution with the free amino group of an amino thioester. This furnishes the fully protected peptide thioester, which can be globally deprotected to afford the desired unprotected peptide thioester.

Original language	English
Journal	European Journal of Organic Chemistry
Volume	2013
Issue number	24
Pages (from-to)	5290-5294
Number of pages	5
ISSN	1434-193X
DOIs	https://doi.org/10.1002/ejoc.201300927
Publication status	Published - 1 Aug 2013

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10.1002/ejoc.201300927

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title = "Preparation of peptide thioesters through fmoc-based solid-phase peptide synthesis by using amino thioesters",

abstract = "An effective procedure for the synthesis of peptide alkyl thioesters by 9-fluorenylmethoxycarbonyl (Fmoc) solid-phase peptide synthesis was developed. The free C terminus of a fully protected peptide was coupled in solution with the free amino group of an amino thioester. This furnished the fully protected peptide thioester, which was globally deprotected to afford the desired unprotected peptide thioester. The method is compatible with labile groups such as phosphoryl and glycosyl moieties. The synthesis of peptide alkyl thioesters by 9-fluorenylmethoxycarbonyl (Fmoc) solid-phase peptide synthesis (SPPS) is developed. The free C terminus of a fully protected peptide is coupled in solution with the free amino group of an amino thioester. This furnishes the fully protected peptide thioester, which can be globally deprotected to afford the desired unprotected peptide thioester.",

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T1 - Preparation of peptide thioesters through fmoc-based solid-phase peptide synthesis by using amino thioesters

AU - Stuhr-Hansen, N.

AU - Wilbek, T.S.

AU - Strømgaard, K.

PY - 2013/8/1

Y1 - 2013/8/1

N2 - An effective procedure for the synthesis of peptide alkyl thioesters by 9-fluorenylmethoxycarbonyl (Fmoc) solid-phase peptide synthesis was developed. The free C terminus of a fully protected peptide was coupled in solution with the free amino group of an amino thioester. This furnished the fully protected peptide thioester, which was globally deprotected to afford the desired unprotected peptide thioester. The method is compatible with labile groups such as phosphoryl and glycosyl moieties. The synthesis of peptide alkyl thioesters by 9-fluorenylmethoxycarbonyl (Fmoc) solid-phase peptide synthesis (SPPS) is developed. The free C terminus of a fully protected peptide is coupled in solution with the free amino group of an amino thioester. This furnishes the fully protected peptide thioester, which can be globally deprotected to afford the desired unprotected peptide thioester.

AB - An effective procedure for the synthesis of peptide alkyl thioesters by 9-fluorenylmethoxycarbonyl (Fmoc) solid-phase peptide synthesis was developed. The free C terminus of a fully protected peptide was coupled in solution with the free amino group of an amino thioester. This furnished the fully protected peptide thioester, which was globally deprotected to afford the desired unprotected peptide thioester. The method is compatible with labile groups such as phosphoryl and glycosyl moieties. The synthesis of peptide alkyl thioesters by 9-fluorenylmethoxycarbonyl (Fmoc) solid-phase peptide synthesis (SPPS) is developed. The free C terminus of a fully protected peptide is coupled in solution with the free amino group of an amino thioester. This furnishes the fully protected peptide thioester, which can be globally deprotected to afford the desired unprotected peptide thioester.

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JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 24

ER -

Preparation of peptide thioesters through fmoc-based solid-phase peptide synthesis by using amino thioesters

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