Open AccessStructure of Ristocetin A
Author(s) -
James R. Fehlner,
R. E. J. Hutchinson,
D. S. Tarbell,
Jay R. Schenck
Publication year - 1972
Publication title -
proceedings of the national academy of sciences of the united states of america
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.011
H-Index - 771
eISSN - 1091-6490
pISSN - 0027-8424
DOI - 10.1073/pnas.69.9.2420
Subject(s) - diastereomer , chemistry , ring (chemistry) , acid hydrolysis , ether , stereochemistry , amino acid , hydrolysis , diphenyl ether , organic chemistry , biochemistry
Acid hydrolysis of ristocein A yields a number of amino acids of unusual structure. One set of diastereoisomeric pairs has a molecular weight of 362 and an empirical formula of C17 H18 N2 O7 . Mass spectral and nuclear magnetic resonance (NMR) evidence suggest a diphenyl ether with hydroxyl and α-amino acid [-CH-(NH2 )COOH] groups on one ring, and methyl, hydroxyl and α-amino acid groups on the other ring. Coupling in the NMR and nuclear Overhauser effect experiments favor certain substitution patterns, which are shown. Another set of diastereoisomers seems to be a lower homolog of the previous set, without the aromatic methyl group.