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

TY - JOUR

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.

UR - http://www.scopus.com/inward/record.url?scp=84881665816&partnerID=8YFLogxK

U2 - 10.1002/ejoc.201300927

DO - 10.1002/ejoc.201300927

M3 - Journal article

AN - SCOPUS:84881665816

SN - 1434-193X

VL - 2013

SP - 5290

EP - 5294

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 24

ER -