Biosynthesis of riboflavin: mechanism of formation of the ribitylamino linkage

Journal Article · Mon Feb 22 23:00:00 EST 1988 · Biochemistry; (United States)

DOI:https://doi.org/10.1021/bi00404a006· OSTI ID:5272366

Keller, P J; Van, Q L; Kim, S U; Bown, D H; Chen, H C; Kohnle, A; Bacher, A; Floss, H G

Feeding experiments with Ashbya gossypii followed by NMR analysis of the resulting riboflavin showed incorporation of deuterium from D-(2-/sup 2/H)ribose at C-2' and from D-(1-/sup 2/H) ribose in the pro-R position at C-1' of the ribityl side chain. The results rule out an Amadori rearrangement mechanism for the reduction of the ribosylamino to the ribitylamino linkage and point to formation of a Schiff base that is reduced stereospecifically opposite to the face from which the oxygen has departed. As prerequisite for the analysis, the /sup 1/H NMR signals for the pro-R and pro-S hydrogens at C-1' of 6,7-dimethyl-8-ribityllumazine and riboflavin and its tetraacetate were assigned with the aid of synthetic stereospecifically deuteriated samples.

• Research Organization: Ohio State Univ., Columbus (USA)
• OSTI ID: 5272366
• Journal Information: Biochemistry; (United States), Journal Name: Biochemistry; (United States) Vol. 27:4; ISSN BICHA
• Country of Publication: United States
• Language: English

Related Subjects

550201* -- Biochemistry-- Tracer Techniques
59 BASIC BIOLOGICAL SCIENCES
BARYONS
BIOSYNTHESIS
DEUTERIUM COMPOUNDS
ELEMENTARY PARTICLES
FERMIONS
HADRONS
HYDROGEN COMPOUNDS
IMINES
MAGNETIC RESONANCE
NUCLEAR MAGNETIC RESONANCE
NUCLEONS
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
PROTONS
RESONANCE
RIBOFLAVIN
SCHIFF BASES
SYNTHESIS
UPTAKE
VITAMIN B GROUP
VITAMINS