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The C-Terminal O-S Acyl Shift Pathway under Acidic Condition to Propose Peptide-Thioesters.

ABSTRACT: Peptide-thioester is a pivotal intermediate for peptide ligation and N-, C-terminal cyclization. In this study, desired pathway and the side products of two C-terminal handles, hydroxyethylthiol (HET) and hydroxypropylthiol (HPT) are described in different conditions as well as kinetic studies. In addition, a new mechanism of C-terminal residue racemization is proposed on the basis of differentiation of products derived from the two C-terminal handles in preparing peptide thioesters through an acid-catalyzed tandem thiol switch, first by an intramolecular O-S acyl shift, and then by an intermolecular S-S exchange.

SUBMITTER: Kim BM

PROVIDER: S-EPMC6272864 | biostudies-other | 2016 Nov

REPOSITORIES: biostudies-other

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The C-Terminal O-S Acyl Shift Pathway under Acidic Condition to Propose Peptide-Thioesters.

Kim Bo Mi BM

Molecules (Basel, Switzerland) 20161117 11

Peptide-thioester is a pivotal intermediate for peptide ligation and N-, C-terminal cyclization. In this study, desired pathway and the side products of two C-terminal handles, hydroxyethylthiol (HET) and hydroxypropylthiol (HPT) are described in different conditions as well as kinetic studies. In addition, a new mechanism of C-terminal residue racemization is proposed on the basis of differentiation of products derived from the two C-terminal handles in preparing peptide thioesters through an a ...[more]

PMID: 27869694

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