ISSN:
0170-2041
Keywords:
N-Valyl-dihydroxyhomoproline
;
Streptomyces antibioticus ssp. Tü 1718 B
;
Antibiotics
;
Peptides
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Two stereoisomers (1a and 1b) of N-(L-valyl)-2′,5-dihydroxyhomoproline, the proposed structure of the dipeptide antibiotic Tü 1718 B, were synthesized by starting from natural (2S,4R)-hydroxyproline. The 1H- and 13C-NMR spectra of 1a and 1b clearly differ from the corresponding spectra of the natural product. From both synthetic stereoisomers characteristic mass spectra were obtained after esterification and trifluoroacetylation. Isomer 1a is present as a mixture of two stable conformers, as indicated by peak splitting in the1H-NMR spectra, which disappears at higher temperature, while 1b exits as a single conformer. Both synthetic stereoisomers are antibiotically inactive.
Additional Material:
2 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.1992199201212
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