Open AccessSTEREOCHEMISTRY OF NUCLEIC ACIDS AND THEIR CONSTITUENTS, XI. THE CONFORMATION OF THE ANTIBIOTIC PUROMYCIN DIHYDROCHLORIDE PENTAHYDRATE
Author(s) -
M. Sundaralingam,
S. K. Arora
Publication year - 1969
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.64.3.1021
Subject(s) - nucleic acid , stereochemistry , puromycin , chemistry , hydrogen bond , phenylalanine , nucleoside , nucleotide , tyrosine , enzyme , peptide bond , molecule , biochemistry , crystallography , amino acid , protein biosynthesis , organic chemistry , gene
The elucidation of puromycin structure represents the first case where both a nucleic acid and a protein fragment are found together in a crystal. The molecule displays an elongated conformation with the nucleoside and thep -methoxy-L-phenylalanine in the preferred conformation. The purine and the tyrosine rings form alternating stacks with interplanar spacings of 3.4 Å. The inhibitory effect of this antiobiotic may be due, in part, to its unique conformation and the ability of the amide proton on N(3′) to hydrogen bond to the active site of the ribosomal enzyme, peptide synthetase.