Isomer-sensitive deboronation in reductive aminations of aryl boronic acids

Journal Article · Sat Sep 05 00:00:00 EDT 2015 · Tetrahedron Letters

DOI:https://doi.org/10.1016/j.tetlet.2015.09.006· OSTI ID:1236230

Jones, Brad Howard ^[1]; Wheeler, David R. ^[1]; Wheeler, Jill S. ^[1]; Miller, Lance Lee ^[1]; Alam, Todd M. ^[1]; Spoerke, Erik David ^[1]

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1. Sandia National Lab. (SNL-NM), Albuquerque, NM (United States)

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.

• Research Organization: Sandia National Laboratories (SNL-NM), Albuquerque, NM (United States)
• Sponsoring Organization: USDOE; USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
• Grant/Contract Number: AC04-94AL85000
• OSTI ID: 1236230
• Alternate ID(s): OSTI ID: 1245652
• Report Number(s): SAND--2015-7544J; 603484
• Journal Information: Tetrahedron Letters, Journal Name: Tetrahedron Letters Journal Issue: C Vol. 56; ISSN 0040-4039
• Publisher: Elsevier
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
boronic acid
deboronation
formylphenylboronic acid
peptide modification
reductive amination