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The synthesis and analysis of the conformation in solution of the dolastatin 3 diastereomer cyclo[-L-Pro-L-Leu-D-(Gln)Thz-(Gly)Thz-L-Val-]

✍ Scribed by Bredenkamp, Martin W. ;Holzapfel, Cedric W. ;van Zyl, Wynand J.

Book ID
102901333
Publisher
John Wiley and Sons
Year
1990
Tongue
English
Weight
525 KB
Volume
1990
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

The cyclic peptide cyclo[‐L‐Pro‐L‐Leu‐D‐(Gln)Thz‐(Gly)Thz‐L‐Val‐] (1a), which is a diastereomer of the antineoplastic agent dolastatin 3 (1b), and contains the unusual thiazole amino acids, was synthesized. All the peptide bonds of the cyclic peptide 1a are trans in solution, and the compound is conformationally homogeneous, as deduced by CD spectroscopy and comprehensive NMR spectroscopy. The conformation was refined by SYBYL molecular force‐field calculations. The saddle‐like conformation contains three intramolecular, but no transannular hydrogen bonds.

📜 SIMILAR VOLUMES

The synthesis and conformation in soluti
The synthesis and conformation in solution of cyclo[L-pro-L-leu-(gln)thz-(gly)thz-L-val] (dolastatin 3)
✍ Cedric W. Holzapfel; Wynand J. van Zyl; Marita Roos 📂 Article 📅 1990 🏛 Elsevier Science 🌐 French ⚖ 788 KB

Ah&act: Dolastatin 3, a unique cyclic peptide, was synthesised in hi h yield. Its minimum energy conformation in solution was established by NMR spectroscopy and force ield calculations, and is character&d k by three intramolecular hydrogen bonds.