Reaction: S-adenosyl-L-methionine + NAD+ = S-methyl-5'-thioadenosine + (4aR,7S)-2-(adenosyl(5')diphospho(5)ribosyl)-7-amino-4-carbamoyl-4a,5,6,7-tetrahydro-2H-cyclopenta[c]pyridine-7-carboxylate
Glossary: S-methyl-5'-thioadenosine = 5'-methylthioadenosine
SB-203207 = (sulfonamide-N)(L-isoleucyl)altemidicin = (4aR,6S,7R,7aS)-4-(carbamoyl)-7-({[(2S,3S)-2-amino-3-methylpentanoyl]aminosulphonyl}acetamido)-6-hydroxy-2-methyl-1,4a,5,6,7,7a-hexahydro-2H-cyclopenta[c]pyrindine-7-carboxylate
SB-203208 = (4aR,6S,7R,7aS)-4-(carbamonyl)-7-({[(2S,3S)-2-amino-3-methylpentanoyl]-aminosulphonyl}acetamido)-6-{[(2S,3S)-2-amino-3-phenylbutanoyl]oxy}-2-methyl-1,4a,5,6,7,7a-hexahydro-2H-cyclopents[c]pyrindine-7-carboxylate
Other name(s): sbzP (gene name)
Systematic name: S-adenosyl-L-methionine:NAD+ aminocarboxypropyltransferase
Comments: The enzyme, isolated from the bacterium Streptomyces sp. NCIMB40513, participates in the biosynthesis of the monoterpene alkaloids altemicidin, SB-203207 and SB-203208.The enzyme catalyses a pyridoxal phosphate-dependent [3+2]-annulation reaction between S-adenosyl-L-methionine (SAM) and NAD+. It transfers an aminocarboxypropyl group that combines with the pyridinium moiety of NAD+ to create a pentacyclic ring, forming a 6-azatetrahydroindane scaffold.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc, CAS registry number:
References:
1. Barra, L., Awakawa, T., Shirai, K., Hu, Z., Bashiri, G. and Abe, I. β-NAD as a building block in natural product biosynthesis. Nature 600 (2021) 754-758. [PMID: 34880494]