Construction of Thioamide Peptide via Sulfur-Involved Amino Acids/Amino Aldehydes Coupling

Yanyan Liao; Xuefeng Jiang

doi:10.1021/acs.orglett.1c03370

Construction of Thioamide Peptide via Sulfur-Involved Amino Acids/Amino Aldehydes Coupling

Yanyan Liao, Xuefeng Jiang

School of Chemistry and Molecular Engineering

Research output: Contribution to journal › Article › peer-review

30 Scopus citations

Abstract

A sulfur-involved ligation for thioamide quasi-peptides was developed via amino acids and amino aldehydes coupling. The key to the transformation was the chelation of copper with imines for chiral activation and fixation. In this environment, linear polysulfur decreased the alkalinity of single sulfur anions to prevent racemization caused by the interaction between sulfur and sodium sulfide. Dipeptides, tripeptides, tetrapeptides, and the linkage between the drug and amino acids were successfully obtained.

Original language	English
Pages (from-to)	8862-8866
Number of pages	5
Journal	Organic Letters
Volume	23
Issue number	22
DOIs	https://doi.org/10.1021/acs.orglett.1c03370
State	Published - 19 Nov 2021

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abstract = "A sulfur-involved ligation for thioamide quasi-peptides was developed via amino acids and amino aldehydes coupling. The key to the transformation was the chelation of copper with imines for chiral activation and fixation. In this environment, linear polysulfur decreased the alkalinity of single sulfur anions to prevent racemization caused by the interaction between sulfur and sodium sulfide. Dipeptides, tripeptides, tetrapeptides, and the linkage between the drug and amino acids were successfully obtained.",

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Y1 - 2021/11/19

N2 - A sulfur-involved ligation for thioamide quasi-peptides was developed via amino acids and amino aldehydes coupling. The key to the transformation was the chelation of copper with imines for chiral activation and fixation. In this environment, linear polysulfur decreased the alkalinity of single sulfur anions to prevent racemization caused by the interaction between sulfur and sodium sulfide. Dipeptides, tripeptides, tetrapeptides, and the linkage between the drug and amino acids were successfully obtained.

AB - A sulfur-involved ligation for thioamide quasi-peptides was developed via amino acids and amino aldehydes coupling. The key to the transformation was the chelation of copper with imines for chiral activation and fixation. In this environment, linear polysulfur decreased the alkalinity of single sulfur anions to prevent racemization caused by the interaction between sulfur and sodium sulfide. Dipeptides, tripeptides, tetrapeptides, and the linkage between the drug and amino acids were successfully obtained.

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DO - 10.1021/acs.orglett.1c03370

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Construction of Thioamide Peptide via Sulfur-Involved Amino Acids/Amino Aldehydes Coupling

Abstract

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