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Key analogs of the tetrapeptide subunit of RA-VII and deoxybouvardin

Academic Article
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Overview

related to degree

  • Zhou, Jiacheng, Ph.D. in Chemistry, Scripps Research 1991 - 1996

authors

  • Boger, Dale
  • Zhou, Jiacheng
  • Winter, B.
  • Kitos, P. A.

publication date

  • December 1995

journal

  • Bioorganic & Medicinal Chemistry  Journal

abstract

  • The synthesis and evaluation of two key analogs 3 and 4 of the potent antitumor antibiotics deoxybouvardin (1) and RA-VII (2) which contain fundamental modifications in the tetrapeptide subunit are described. Unlike the natural products, these agents 3 and 4, which substitute (Gly)4 and (Gly)3 for the D-Ala-Ala-NMe-Tyr(OMe)-Ala tetrapeptide subunit, adopt conformations in which the central amide in the cycloisodityrosine subunit adopts its inherently preferred trans stereochemistry and both were found to be biologically inactive.

subject areas

  • Amino Acid Sequence
  • Antibiotics, Antineoplastic
  • Antineoplastic Agents, Phytogenic
  • Crystallography, X-Ray
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Conformation
  • Molecular Sequence Data
  • Molecular Structure
  • Peptides, Cyclic
  • Stereoisomerism
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Identity

International Standard Serial Number (ISSN)

  • 0968-0896

Digital Object Identifier (DOI)

  • 10.1016/0968-0896(95)00141-7

PubMed ID

  • 8770383
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Additional Document Info

start page

  • 1579

end page

  • 1593

volume

  • 3

issue

  • 12

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