Configurational and conformational studies on the group A peptide antibiotics of the mikamycin (streptogramin, virginiamycin) family
- 1 January 1977
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 22,p. 2464-2470
- https://doi.org/10.1039/p19770002464
Abstract
The crystal conformations of griseoviridin (3) and ostreogrycin A (5), which are shown to bear a close resemblance over a large part of the macrocycle, have been compared with those adopted in solution. It is concluded, on the basis of 13C and 1H n.m.r. as well as i.r. data, that one predominant solution conformer exists for both molecules which is essentially the same as that adopted in the crystal lattice. An earlier claim that ostreogrycin A is stabilised by an intramolecular hydrogen bond is reviewed. Spectral data on madumycin (A2315) are used to confirm the proposed structure (6) and comparisons with compounds (3) and (5) have allowed tentative assignments of the relative configuration and the ring conformation. Absolute configurational assignments are made for compounds (5) and (6) and the significance of the molecular geometry of the group is discussed.This publication has 3 references indexed in Scilit:
- Berninamycin. 2. Products of acidic hydrolysis, methanolysis, and acetolysis of berninamycin AJournal of the American Chemical Society, 1976
- Structure of the antibiotic griseoviridinJournal of the American Chemical Society, 1976
- Revised constitution, absolute configuration, and conformation of griseoviridin, a modified cyclic peptide antibioticJournal of the Chemical Society, Perkin Transactions 1, 1976