6,7-Dimethyl-8-ribityllumazine → Riboflavin

HRID 399375

Reaction equation

P(O[CH2:14][C@H:15]1O[C@@H](N2C3N=C(N)NC(=O)C=3N=C2)[C@H:17](O)[C@@H:16]1O)(OP(OP(O)(O)=O)(O)=O)(=O)O.C(NC1NC(=O)NC(=O)C=1N)[C@H](O)[C@H](O)[C@H](O)CO.[CH3:52][C:53]1[N:64]=[C:63]2[C:56](=[N:57][C:58]([NH:60][C:61]2=[O:62])=[O:59])[N:55]([CH2:65][C@H:66]([OH:73])[C@H:67]([OH:72])[C@H:68]([OH:71])[CH2:69][OH:70])[C:54]=1[CH3:74]>>[CH3:14][C:15]1[CH:52]=[C:53]2[N:64]=[C:63]3[C:56](=[N:57][C:58]([NH:60][C:61]3=[O:62])=[O:59])[N:55]([CH2:65][C@H:66]([OH:73])[C@H:67]([OH:72])[C@H:68]([OH:71])[CH2:69][OH:70])[C:54]2=[CH:74][C:16]=1[CH3:17]

Participants

Reactant 3

HCID 1689896,7-Dimethyl-8-ribityllumazine

HCID 1935165-amino-6-(D-ribitylamino)uracil

HCID 135398633Guanosine Triphosphate2×

Product 1

HCID 493570Riboflavin

Procedure

Guanosine triphosphate (GTP) is converted by GTP cyclohydrolase II (rib 1 gene product) into 2,5-diamino-6-ribosylamino-4(3H)-pyrimidinone 5-phosphate. This compound is subsequently reduced by the rib 7 gene product to 2,5-diaminoribitylamino-2,4(1H,3H)-pyrimidine 5-phosphate and then deaminated by the rib 2 gene product to 5-amino-6-ribitylamino-2,4(1H,3H)-pyrimidinedione. Subsequently, in a reaction catalyzed by the rib 4 gene product, the C4 compound DBP is added on to result in 6,7-dimethyl-8-ribitvllumazine (DMRL), from which riboflavin is produced in the reaction catalyzed by the rib 5 gene product. The C4 compound DBP (L-3,4-dihydroxy-2-butanone 4-phosphate) is formed from D-ribulose 5-phosphate in a reaction catalyzed by the rib 3 gene product.

Workup

additionthe C4 compound DBP is added on

Sources & evidence

ORD record: ord-b9b00209e872409aaf7e4c3653bfc816
Source dataset: uspto-grants-1998_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05821090

Linked notes

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