1417697-27-8

Basic information

• Product Name: C₃₅H₅₂O₃S
• CAS NO: 1417697-27-8
• Molecular Weight: 552.862
• Mol File: 1417697-27-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: C₃₅H₅₂O₃S(CAS DataBase Reference)
• NIST Chemistry Reference: C₃₅H₅₂O₃S(1417697-27-8)
• EPA Substance Registry System: C₃₅H₅₂O₃S(1417697-27-8)

Safety Data

• Hazardous Substances Data: 1417697-27-8(Hazardous Substances Data)

Upstream product

• 1417697-26-7 (E)-3,8-dibromo-2,6-dimethyloct-6-en-2-ol 
• 130826-83-4 (E)-6-bromo-3,7-dimethyloct-2-ene-1,7-diol 
• 106-24-1 Geraniol 
• 74832-85-2 6,7-oxido-3,7-dimethyl-1-(benzenesulfonyl)-(2E)-octene 

Relevant articles and documents

Lanosterol biosynthesis: The critical role of the methyl-29 group of 2,3-oxidosqualene for the correct folding of this substrate and for the construction of the five-membered D ring

Lanosterol synthase catalyzes the polycyclization reaction of (3S)-2,3-oxidosqualene (1) into tetracyclic lanosterol 2 by folding 1 in a chair-boat-chair-chair conformation. 27-Nor- and 29-noroxidosqaulenes (7 and 8, respectively) were incubated with this enzyme to investigate the role of the methyl groups on 1 for the polycyclization cascade. Compound 7 afforded two enzymatic products, namely, 30-norlanosterol (12) and 26-normalabaricatriene (13; 12/13 9:1), which were produced through the normal chair-boat-chair-chair conformation and an atypical chair-chair-boat conformation, respectively. Compound 8 gave two products 14 and 15 (14/15 4:5), which were generated by the normal and the unusual polycyclization pathways through a chair-chair-boat-chair conformation, respectively. It is remarkable that the twist-boat structure for the B-ring formation was changed to an energetically favored chair structure for the generation of 15. Surprisingly, 14 and 15 consisted of a novel 6,6,6,6-fused tetracyclic ring system, thus differing from the 6,6,6,5-fused lanosterol skeleton. Together with previous results, we conclude that the methyl-29 group is critical to the correct folding of 1, with lesser contributions from the other branched methyl groups, such as methyl-26, -27, and -28. Furthermore, we demonstrate that the methyl-29 group has a crucial role in the formation of the five-membered D ring of the lanosterol scaffold. Ringing in the changes: The incubation of 1 with porcine-liver cyclase afforded new nortriterpenes 2 and 3 with 6,6,6,6-fused tetracyclic skeletons, which were produced by chair-boat-chair-chair and chair-chair-boat-chair conformations, respectively (see scheme), thus indicating that the 29-methyl group is critical to the correct folding of oxidosqualene and to the formation of the five-membered D ring for lanosterol biosynthesis. Copyright