7-Deazapurine biosynthesis: NMR study of toyocamycin biosynthesis in Streptomyces rimosus using 2-C-13-7-N-15-adenine

Although 7-deazapurines are well known and feature in the hypermodified RNA base queuosine, and in a range of nucleoside antibiotics such as toyocamycin, a mechanistic understanding of their biosynthesis is a longstanding problem. In particular, the obligatory loss of the N-7 nitrogen atom is puzzli...

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Published inOrganic & biomolecular chemistry Vol. 9; no. 7; pp. 2227 - 2232
Main Authors Battaglia, Ugo, Long, Jed E., Searle, Mark S., Moody, Christopher J.
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.01.2011
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ANTIBIOTICS
ORIGIN
QUEF
ACID
RNA
PYRROLOPYRIMIDINE NUCLEOSIDES
BACILLUS-SUBTILIS
PATHWAY
OXIDOREDUCTASE
CYCLOHYDROLASE
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Summary:Although 7-deazapurines are well known and feature in the hypermodified RNA base queuosine, and in a range of nucleoside antibiotics such as toyocamycin, a mechanistic understanding of their biosynthesis is a longstanding problem. In particular, the obligatory loss of the N-7 nitrogen atom is puzzling, and in order to address this mechanistic conundrum a novel doubly labeled purine, [2-C-13, 7-N-15]-adenine, has been prepared and used as a biosynthetic precursor to toyocamycin in Streptomyces rimosus. NMR spectroscopy and mass spectrometry clearly showed incorporation of C-13 but loss of N-15 in the toyocamycin produced.
ISSN:1477-0520
1477-0539
DOI:10.1039/c0ob01054e