Investigations of the biosynthesis of sparsomycin

Thesis/Dissertation · Fri Jan 01 04:00:00 EST 1988

OSTI ID:5228050

Gomez, M E.E.

Investigations of the biosynthesis of the antitumor antibiotic sparsomycin (1) by Streptomyces sparsogenes have been carried out. Incorporation studies employing ({sup 13}C)-labeled precursors have shown that the monoxodithioacetal moiety (6) of the antibiotic arises from the stepwise introduction of a thiomethyl group into the S-methyl group of S-methyl-D-cysteine. The methyl group of (6) has its origin in the methyl group of L-methionine, but an experiment utilizing (methyl-{sup 3}H,{sup 35}S)-L-methionine has demonstrated that intact incorporation of the thiomethyl group of this precursor does not occur. The results of feeding experiments with ({sup 13}C)- and ({sup 2}H)-labeled forms of tryptophan have indicated that the uracil moiety (7) of sparsomycin is derived from the indole nucleus of tryptophan via aromatic ring cleavage followed by recyclization. Preliminary evidence for the intermediacy of N-formyl-anthranilic acid in the conversion of tryptophan to sparsomycin has been obtained.

• Research Organization: Rice Univ., Houston, TX (USA)
• OSTI ID: 5228050
• Country of Publication: United States
• Language: English

Related Subjects

550201* -- Biochemistry-- Tracer Techniques
59 BASIC BIOLOGICAL SCIENCES
AMINO ACIDS
ANTI-INFECTIVE AGENTS
ANTIBIOTICS
BACTERIA
BETA DECAY RADIOISOTOPES
BETA-MINUS DECAY RADIOISOTOPES
BIOSYNTHESIS
CARBON 13
CARBON ISOTOPES
CARBOXYLIC ACIDS
DAYS LIVING RADIOISOTOPES
DEUTERIUM
DRUGS
EVEN-ODD NUCLEI
HYDROGEN COMPOUNDS
HYDROGEN ISOTOPES
ISOTOPE APPLICATIONS
ISOTOPES
LIGHT NUCLEI
LIPOTROPIC FACTORS
METHIONINE
MICROORGANISMS
NUCLEI
ODD-ODD NUCLEI
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC SULFUR COMPOUNDS
PRECURSOR
RADIOISOTOPES
STABLE ISOTOPES
STREPTOMYCES
SULFUR 35
SULFUR ISOTOPES
SYNTHESIS
TRACER TECHNIQUES
TRITIUM COMPOUNDS