Isomer-sensitive deboronation in reductive aminations of aryl boronic acids

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

doi:10.1016/j.tetlet.2015.09.006

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

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Abstract

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:

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

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

Publication Date:: Sat Sep 05 00:00:00 EDT 2015

Research Org.:: Sandia National Lab. (SNL-NM), Albuquerque, NM (United States)

Sponsoring Org.:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

OSTI Identifier:: 1236230

Alternate Identifier(s):: OSTI ID: 1245652

Report Number(s):: SAND-2015-7544J
Journal ID: ISSN 0040-4039; 603484

Grant/Contract Number:: AC04-94AL85000

Resource Type:: Accepted Manuscript

Journal Name:: Tetrahedron Letters

Additional Journal Information:: Journal Volume: 56; Journal Issue: C; Journal ID: ISSN 0040-4039

Publisher:: Elsevier

Country of Publication:: United States

Language:: English

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

Citation Formats


                    Jones, Brad Howard, Wheeler, David R., Wheeler, Jill S., Miller, Lance Lee, Alam, Todd M., and Spoerke, Erik David. Isomer-sensitive deboronation in reductive aminations of aryl boronic acids.  United States: N. p., 2015. 
Web.  doi:10.1016/j.tetlet.2015.09.006.

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                    Jones, Brad Howard, Wheeler, David R., Wheeler, Jill S., Miller, Lance Lee, Alam, Todd M., & Spoerke, Erik David. Isomer-sensitive deboronation in reductive aminations of aryl boronic acids.  United States.  https://doi.org/10.1016/j.tetlet.2015.09.006

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                    Jones, Brad Howard, Wheeler, David R., Wheeler, Jill S., Miller, Lance Lee, Alam, Todd M., and Spoerke, Erik David. Sat .  
"Isomer-sensitive deboronation in reductive aminations of aryl boronic acids".  United States.  https://doi.org/10.1016/j.tetlet.2015.09.006.  https://www.osti.gov/servlets/purl/1236230.

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@article{osti_1236230,

  title        = {Isomer-sensitive deboronation in reductive aminations of aryl boronic acids},

  author       = {Jones, Brad Howard and Wheeler, David R. and Wheeler, Jill S. and Miller, Lance Lee and Alam, Todd M. and Spoerke, Erik David},

  abstractNote = {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.},

  doi          = {10.1016/j.tetlet.2015.09.006},

  journal      = {Tetrahedron Letters},

  number       = C,

  volume       = 56,

  place        = {United States},

  year         = {Sat Sep 05 00:00:00 EDT 2015},

  month        = {Sat Sep 05 00:00:00 EDT 2015}

}

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