Synthesis of a phosphorothioate derivative of flavin mononucleotide

Conference · Fri May 01 04:00:00 EDT 1987 · Fed. Proc., Fed. Am. Soc. Exp. Biol.; (United States)

OSTI ID:6359823

Calhoun, J P; Miziorko, H M; Otvos, J D; Masters, B S.S.

The synthesis of riboflavin-5'-phosphorothioate (5'-FMNS), an analog of riboflavin-5'-phosphate (FMN), is described. 5'-FMNS is produced from the alkaline hydrolysis of riboflavin-4',5'-cyclic phosphorothioate (cFMNS). The cyclic phosphorothioate is produced upon reaction of riboflavin with thiophosphoryl chloride in trimethyl phosphate. The phosphorothioate compounds have been characterized by TC and T P NMR and the purified 5'-FMNS is isolated by preparative HPLC. Preliminary results indicate that this analog of FMN is capable of replacing FMN in at least on flavoprotein, NADPH-cytochrome P-450 reductase, and is competent in reconstituting the cytochrome c reductase activity of this enzyme. Full characterization of this derivatized flavoprotein is in progress.

• Research Organization: Medical College of Wisconsin, Milwaukee
• OSTI ID: 6359823
• Report Number(s): CONF-870644-
• Conference Information: Journal Name: Fed. Proc., Fed. Am. Soc. Exp. Biol.; (United States) Journal Volume: 46:6
• Country of Publication: United States
• Language: English

Related Subjects

550201* -- Biochemistry-- Tracer Techniques
59 BASIC BIOLOGICAL SCIENCES
CARBON 13
CARBON ISOTOPES
CHEMICAL PREPARATION
CHROMATOGRAPHY
EVEN-ODD NUCLEI
ISOTOPES
LIGHT NUCLEI
LIQUID COLUMN CHROMATOGRAPHY
MAGNETIC RESONANCE
NMR SPECTRA
NUCLEAR MAGNETIC RESONANCE
NUCLEI
ODD-EVEN NUCLEI
ORGANIC COMPOUNDS
ORGANIC PHOSPHORUS COMPOUNDS
PHOSPHORUS 31
PHOSPHORUS ISOTOPES
RESONANCE
SEPARATION PROCESSES
SPECTRA
STABLE ISOTOPES
SYNTHESIS