Campus Units
Chemistry
Document Type
Article
Publication Version
Submitted Manuscript
Publication Date
12-6-2019
Journal or Book Title
The Journal of Organic Chemistry
Volume
84
Issue
23
First Page
15309
Last Page
15314
DOI
10.1021/acs.joc.9b02317
Abstract
Thioamides are important biophysical probes of peptide folding but are prone to α-C epimerization during Fmoc solid-phase peptide synthesis. The stereochemical integrity of thioamide-containing peptides can be dramatically improved by protecting the thioamide as a thioimidate during synthesis. A drawback of this approach, however, is that once synthesis of the peptide is complete, regeneration of the thioamide requires the toxic, corrosive, and flammable gas H2S. This work examines several approaches to supplant H2S as a deprotection reagent in favor of a safer and more convenient alternative. Ultimately, a new application of the 4-azidobenzyl protecting group to thioamides was found to provide the most suitable means of both protection of α-C stereochemistry and conversion back to thioamide.
Copyright Owner
American Chemical Society
Copyright Date
2019
Language
en
File Format
application/pdf
Recommended Citation
Camacho, Luis A. III; Nguyen, Yen H.; Turner, John; and VanVeller, Brett, "Deprotection Strategies for Thioimidates during Fmoc Solid-Phase Peptide Synthesis: A Safe Route to Thioamides" (2019). Chemistry Publications. 1275.
https://lib.dr.iastate.edu/chem_pubs/1275
Comments
This document is the unedited Author’s version of a Submitted Work that was subsequently accepted for publication in The Journal of Organic Chemistry, copyright © American Chemical Society after peer review. To access the final edited and published work see DOI: 10.1021/acs.joc.9b02317. Posted with permission.