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Synthesis of all nineteen appropriately protected chiral alpha-hydroxy acid equivalents of the alpha-amino acids for Boc solid-phase depsi-peptide synthesis

Academic Article
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Overview

related to degree

  • Deechongkit, Songpon, Ph.D. in Organic Chemistry, Scripps Research 1999 - 2003

authors

  • Deechongkit, Songpon
  • You, S. L.
  • Kelly, Jeffery

publication date

  • February 2004

journal

  • Organic Letters  Journal

abstract

  • [reaction: see text] The preparation of depsi-peptides, amide-to-ester-substituted peptides used to probe the role of hydrogen bonding in protein folding energetics, is accomplished by replacing specific l-alpha-amino acid residues by their alpha-hydroxy acid counterparts in a solid-phase synthesis employing a t-Boc strategy. Herein we describe the efficient stereoselective synthesis of all 19 appropriately protected alpha-hydroxy acid equivalents of the l-alpha-amino acids, employing commercially available materials, expanding the number of available alpha-hydroxy acids from 9 to 19.

subject areas

  • Amino Acids
  • Catalysis
  • Hydroxy Acids
  • Indicators and Reagents
  • Molecular Structure
  • Peptide Biosynthesis
  • Peptides
  • Stereoisomerism
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Identity

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/ol036102m

PubMed ID

  • 14961607
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Additional Document Info

start page

  • 497

end page

  • 500

volume

  • 6

issue

  • 4

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