Synthesis of Peptide Disulfide-Bond Mimics by Using Fully Orthogonally Protected Diaminodiacids

Tao Wang; Jian Fan; Xiao-Xu Chen; Rui Zhao; Yang Xu; Donald Bierer; Lei Liu; Yi-Ming Li; Jing Shi; Ge-Min Fang

doi:10.1021/acs.orglett.8b02459

Synthesis of Peptide Disulfide-Bond Mimics by Using Fully Orthogonally Protected Diaminodiacids

Org Lett. 2018 Oct 5;20(19):6074-6078. doi: 10.1021/acs.orglett.8b02459. Epub 2018 Sep 14.

Authors

Tao Wang^{1

2}, Jian Fan³, Xiao-Xu Chen¹, Rui Zhao³, Yang Xu³, Donald Bierer⁴, Lei Liu⁵, Yi-Ming Li², Jing Shi³, Ge-Min Fang¹

Affiliations

¹ School of Life Science, Institute of Physical Science and Information Technology , Anhui University , Hefei 230601 , P. R. China.
² School of Biological and Medical Engineering , Hefei University of Technology , Hefei 230009 , P. R. China.
³ Department of Chemistry , University of Science and Technology of China , Hefei 230026 , P. R. China.
⁴ Department of Medicinal Chemistry , Bayer AG , Aprather Weg 18A , 42096 Wuppertal , Germany.
⁵ Tsinghua University , Beijing 100084 , P. R. China.

PMID: 30216082
DOI: 10.1021/acs.orglett.8b02459

Abstract

A new strategy was developed for the synthesis of peptide disulfide-bond mimics using fully orthogonally protected diaminodiacids. This method overcomes the previous problems of heavy-metal contamination and poor compatibility with Fmoc chemistry and provides a practical avenue for the efficient preparation of peptide disulfide-bond mimics.

Publication types

Research Support, Non-U.S. Gov't