20513-97-7

Basic information

• Product Name: (-)-1,2-O-isopropylidene-α-D-5-diphenylphosphoxylofuranose
• Synonyms: (-)-1,2-O-isopropylidene-α-D-5-diphenylphosphoxylofuranose
• CAS NO: 20513-97-7
• Molecular Weight: 422.372
• Mol File: 20513-97-7.mol

Chemical Properties

• CAS DataBase Reference: (-)-1,2-O-isopropylidene-α-D-5-diphenylphosphoxylofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-1,2-O-isopropylidene-α-D-5-diphenylphosphoxylofuranose(20513-97-7)
• EPA Substance Registry System: (-)-1,2-O-isopropylidene-α-D-5-diphenylphosphoxylofuranose(20513-97-7)

Safety Data

• Hazardous Substances Data: 20513-97-7(Hazardous Substances Data)

Upstream product

• 20031-21-4 1,2-O-isopropylidene-α-D-xylose 
• 2524-64-3 chlorophosphoric acid diphenyl ester 
• 58-86-6 D-xylose 
• 20881-04-3 1,2:3,5-di-O-isopropylidene-D-xylofuranose 
• 37077-81-9 1,2-isopropylidene-α-D-ribofuranose 

Relevant articles and documents

Prebiotic synthesis of aminooxazoline-5′-phosphates in water by oxidative phosphorylation

RNA is essential to all life on Earth and is the leading candidate for the first biopolymer of life. Aminooxazolines have recently emerged as key prebiotic ribonucleotide precursors, and here we develop a novel strategy for aminooxazoline-5′-phosphate synthesis in water from prebiotic feedstocks. Oxidation of acrolein delivers glycidaldehyde (90%), which directs a regioselective phosphorylation in water and specifically affords 5′-phosphorylated nucleotide precursors in upto 36% yield. We also demonstrated a generational link between proteinogenic amino acids (Met, Glu, Gln) and nucleotide synthesis.

Construction of the octose 8-phosphate intermediate in lincomycin A biosynthesis: Characterization of the reactions catalyzed by LmbR and LmbN

Lincomycin A is a potent antimicrobial agent noted for its unusual C1 methylmercapto-substituted 8-carbon sugar. Despite its long clinical history for the treatment of Gram-positive infections, the biosynthesis of the C 8-sugar, methylthiolincosamide (MTL), is poorly understood. Here, we report our studies of the two initial enzymatic steps in the MTL biosynthetic pathway leading to the identification of d-erythro-d-gluco-octose 8-phosphate as a key intermediate. Our experiments demonstrate that this intermediate is formed via a transaldol reaction catalyzed by LmbR using d-fructose 6-phosphate or d-sedoheptulose 7-phosphate as the C3 donor and d-ribose 5-phosphate as the C5 acceptor. Subsequent 1,2-isomerization catalyzed by LmbN converts the resulting 2-keto C8-sugar (octulose 8-phosphate) to octose 8-phosphate. These results provide, for the first time, in vitro evidence for the biosynthetic origin of the C8 backbone of MTL.

Arabinose 5-phosphate analogues as mechanistic probes for Neisseria meningitidis 3-deoxy-d-manno-octulosonate 8-phosphate synthase

3-Deoxy-d-manno-octulosonate 8-phosphate (KDO8P) synthase catalyses the condensation reaction between phosphoenolpyruvate and d-arabinose 5-phosphate (d-A5P) in a key step in lipopolysaccharide biosynthesis in Gram-negative bacteria. The KDO8P synthase from Neisseria meningitidis was cloned into Escherichia coli, overexpressed and purified. A variety of d-A5P stereoisomers were tested as substrates, of these only d-A5P and l-X5P were substrates. The Asn59Ala mutant of N. meningitidis KDO8P synthase was constructed and this mutant retained less than 1% of the wild-type activity. These results are consistent with a catalytic mechanism for this enzyme in which the C2 and C3 hydroxyl groups of d-A5P and Asn59 are critical.