Litigation of sidechain unprotected peptides via a masked glycoa

Details Litigation of sidechain unprotected peptides via a masked glycoa Litigation of sidechain unprotected peptides via a masked glycoa

1993-06-21

1996-12-31

Naff, David M.

Chemistry: molecular biology and microbiology

Micro-organism, tissue cell culture or enzyme using process...

Enzymatic production of a protein or polypeptide

530323, 530339, 530345, 530402, C12P 2106, C07K 100, C07K 1107

Patent

active

055893562

ABSTRACT:
A method of chemical ligation of peptides that requires no side chain protecting groups and no activation of the C-.alpha. carboxyl group is presented. The method consists of three steps. In the first step, initiation, a masked glycoaldehyde ester is enzymatically or chemically coupled to the C-terminal carboxylic acid of an sidechain unprotected first peptide. In the second step, ring formation, the masked aldehyde ester of the first peptide is unmasked, and then reacted with the N-.alpha. amino acid of a second sidechain unprotected peptide to form a ring structure. In the third step, rearrangement, the O-acyl ester linkage transfers at higher pH to an N-acyl linkage on the ring to form a peptide bond.

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