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Synthesis and coupling reactions of alpha,alpha-dialkylated amino acids with nucleobase side chains

Academic Article
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Overview

authors

  • Azumaya, I.
  • Aebi, R.
  • Kubik, S.
  • Rebek Jr., Julius

publication date

  • December 1995

journal

  • Proceedings of the National Academy of Sciences of the United States of America  Journal

abstract

  • Several di- and tripeptides containing protected purine (adenine) and pyrimidine (thymine) residues on their side chains were synthesized. The parent amino acids alpha, alpha-dialkylated in a symmetrical manner. An effective coupling procedure was developed for these sterically hindered amino acids: the fluoren-9-ylmethyloxycarbonyl-protected amino acid was dehydrated to its oxazolinone form, which was coupled in good yields with amino esters in hot tetrachloroethane.

subject areas

  • Adenine
  • Alkylation
  • Amino Acids
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Oxazolone
  • Spectrometry, Mass, Fast Atom Bombardment
  • Thymine
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Identity

International Standard Serial Number (ISSN)

  • 0027-8424

Digital Object Identifier (DOI)

  • 10.1073/pnas.92.26.12013

PubMed ID

  • 8618834
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Additional Document Info

start page

  • 12013

end page

  • 12016

volume

  • 92

issue

  • 26

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