Synlett 2018; 29(02): 238-242
DOI: 10.1055/s-0036-1589123
letter
© Georg Thieme Verlag Stuttgart · New York

Homoserine and Threonine Peptide Assembly

Michael C. Pirrung*
a  Department of Chemistry, University of California, Riverside, CA 92521, USA   Email: [email protected]
b  Department of Pharmaceutical Sciences, University of California, Irvine, CA 92697, USA
,
Nicole A. Bakas
a  Department of Chemistry, University of California, Riverside, CA 92521, USA   Email: [email protected]
› Author Affiliations
This work was supported by a grant from the NSF (CHE 1362737).
Further Information

Publication History

Received: 02 August 2017

Accepted after revision: 28.09.2017

Publication Date:
24 October 2017 (online)


Abstract

Drawing on our recent success with reagent-less peptide-bond formation through serine-based assembly reactions in organic solvent, their range has been expanded to threonine and homoserine (an aspartic acid precursor) in the N-terminal peptide. Amino acid scope available at the assembly C-terminus includes bulky residues not amenable to classical ligation methods, such as cysteine-based NCL in aqueous media. The method was used to assemble a snakebite-toxin-neutralizing peptide from opossums.

Supporting Information

 
  • References and Notes

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