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15 N‐NMR Spectroscopy, 15. The Structure of Streptomycin in Solution
Author(s) -
Hull William E.,
Kricheldorf Hans R.
Publication year - 1980
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198019800112
Subject(s) - chemistry , streptomycin , hydrate , aldehyde , nuclear magnetic resonance spectroscopy , aqueous solution , ring (chemistry) , spectroscopy , dihydrostreptomycin , carbon 13 nmr , stereochemistry , organic chemistry , biochemistry , antibiotics , physics , quantum mechanics , catalysis
The natural abundance 15 N‐NMR spectra of streptomycin and dihydrostreptomycin in aqueous solution at pH 5 show conclusively that the aldehyde group of streptomycin does not react with the methylamino or guanidino groups internally to form a four‐ring structure. 13 C‐NMR data provide strong evidence that the aldehyde group forms a hydrate which is stabilized by the hydroxy group at C‐3 of L‐streptose.