132199-98-5

Basic information

• Product Name: (S)-2-(benzyloxy)propanal-1-d
• Synonyms: (S)-2-(benzyloxy)propanal-1-d
• CAS NO: 132199-98-5
• Molecular Weight: 165.196
• Mol File: 132199-98-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (S)-2-(benzyloxy)propanal-1-d(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-(benzyloxy)propanal-1-d(132199-98-5)
• EPA Substance Registry System: (S)-2-(benzyloxy)propanal-1-d(132199-98-5)

Safety Data

• Hazardous Substances Data: 132199-98-5(Hazardous Substances Data)

Upstream product

• 135416-08-9 (S)-(+)-(2)-Benzyloxy-<1,1-²H2>propanol 
• 100-39-0 benzyl bromide 

Downstream Products

• 219474-04-1 (2R,3S)-3-(benzyloxy)-(1,1,1,2-⁽²⁾H₄)butan-2-ol 

Relevant articles and documents

Steric Enforcement of cis-Epoxide Formation in the Radical C-O-Coupling Reaction by Which (S)-2-Hydroxypropylphosphonate Epoxidase (HppE) Produces Fosfomycin

(S)-2-Hydroxypropylphosphonate [(S)-2-HPP, 1] epoxidase (HppE) reduces H2O2 at its nonheme-iron cofactor to install the oxirane "warhead" of the antibiotic fosfomycin. The net replacement of the C1 pro-R hydrogen of 1 by its C2 oxygen, with inversion of configuration at C1, yields the cis-epoxide of the drug [(1R,2S)-epoxypropylphosphonic acid (cis-Fos, 2)]. Here we show that HppE achieves ～95% selectivity for C1 inversion and cis-epoxide formation via steric guidance of a radical-coupling mechanism. Published structures of the HppE·FeII·1 and HppE·ZnII·2 complexes reveal distinct pockets for C3 of the substrate and product and identify four hydrophobic residues - Leu120, Leu144, Phe182, and Leu193 - close to C3 in one of the complexes. Replacement of Leu193 in the substrate C3 pocket with the bulkier Phe enhances stereoselectivity (cis:trans ～99:1), whereas the Leu120Phe substitution in the product C3 pocket diminishes it (～82:18). Retention of C1 configuration and trans-epoxide formation become predominant with the bulk-reducing Phe182Ala substitution in the substrate C3 pocket (～13:87), trifluorination of C3 (～23:77), or both (～1:99). The effect of C3 trifluorination is counteracted by the more constrained substrate C3 pockets in the Leu193Phe (～56:44) and Leu144Phe/Leu193Phe (～90:10) variants. The ability of HppE to epoxidize substrate analogues bearing halogens at C3, C1, or both is inconsistent with a published hypothesis of polar cyclization via a C1 carbocation. Rather, specific enzyme-substrate contacts drive inversion of the C1 radical - as proposed in a recent computational study - to direct formation of the more potently antibacterial cis-epoxide by radicaloid C-O coupling.