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Title: Isomer-sensitive deboronation in reductive aminations of aryl boronic acids

Deboronation is observed during the reductive amination of formylphenylboronic acid (FPBA) to the amine termini and side chains of peptides. This deboronation is sensitive to the isomerism of the boronic acid (BA), with ortho-FPBA yielding complete deboronation in the preparation of an N-terminally-modified dipeptide. The observed behavior is also clearly mediated by the chemical identity of the amine substrate. These results reveal a previously undocumented subtlety of BA functionalization and highlight the importance of thorough spectroscopic characterization in the preparation of peptide and small molecule BAs.
Authors:
 [1] ;  [1] ;  [1] ;  [1] ;  [1] ;  [1]
  1. Sandia National Lab. (SNL-NM), Albuquerque, NM (United States)
Publication Date:
OSTI Identifier:
1236230
Report Number(s):
SAND--2015-7544J
Journal ID: ISSN 0040-4039; 603484
Grant/Contract Number:
AC04-94AL85000
Type:
Accepted Manuscript
Journal Name:
Tetrahedron Letters
Additional Journal Information:
Journal Volume: 56; Journal Issue: C; Journal ID: ISSN 0040-4039
Publisher:
Elsevier
Research Org:
Sandia National Laboratories (SNL-NM), Albuquerque, NM (United States)
Sponsoring Org:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY boronic acid; reductive amination; peptide modification; deboronation; formylphenylboronic acid