Work

The .BETA.-p-nitrobenzyl ester to minimize side reaction during treatment of aspartyl peptides with methanesulfonic acid.

Year: 1978

Type: article

Abstract: When Boc-Asp (OBzl)-Ser (Bzl)-OBzl was deblocked with methanesulfonic acid-anisole to obtain free dipeptide, a few degree of α to β shift was observed. Boc-Asp-(OBzl)-Thr (Bzl)-OBzl had similar property. When β-carboxyl group was protected with p-nitrobenzyl group stable to methanesulfonic acid-anisole, no detectable α to β shift was observed. Boc-Asp (ONb)-Ser (Bzl)-Asp (OBzl)-Pro-Arg (MBS)-ONb was treated with methanesulfonic acid-anisole, followed by catalytic hydrogenation or treatment with zinc powder in acetic acid for the cleavage of p-nitrobenzyl group to give Asp-Ser-Asp-Pro-Arg.

Source: Chemical and Pharmaceutical Bulletin

DOI: 10.1248/cpb.26.2269

Authors: KENJI SUZUKI, NOBUYOSHI ENDO

Language: English

Topic: Chemical Synthesis and Analysis

Subfield: Molecular Biology

Field: Biochemistry, Genetics and Molecular Biology

Domain: Life Sciences

Open Access status: bronze

OpenAlex ID: W1596725637

FWCI: 0.182

Cites:

Cited by: 13

Related to: 10