7284-15-3

Basic information

• Product Name: 2-deoxy-D-ribonic acid
• Synonyms: 2-deoxy-D-ribonic acid
• CAS NO: 7284-15-3
• Molecular Weight: 150.131
• Mol File: 7284-15-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-deoxy-D-ribonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-deoxy-D-ribonic acid(7284-15-3)
• EPA Substance Registry System: 2-deoxy-D-ribonic acid(7284-15-3)

Safety Data

• Hazardous Substances Data: 7284-15-3(Hazardous Substances Data)

Upstream product

• 4134-97-8 3-deoxyglucosone 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 16667-96-2 1,2,5,6-di-O-isopropylidene-α-D-glucofuranose-3-O-(S-methylxanthate) 
• 4613-62-1 3-deoxy-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside 
• 17510-99-5 4,5,6-trihydroxy-2-oxohexanoic acid 
• 10230-17-8 O³-benzyl-D-glucose 
• 50-99-7 D-glucose 
• 533-67-5 2-Deoxy-D-ribose 

Downstream Products

• 110533-61-4 D-erythro-2-deoxy-pentonic acid-(N'-phenyl-hydrazide) 

Relevant articles and documents

Expanding the reaction space of aldolases using hydroxypyruvate as a nucleophilic substrate

Aldolases are key biocatalysts for stereoselective C-C bond formation allowing access to polyoxygenated chiral units through direct, efficient, and sustainable synthetic processes. The aldol reaction involving unprotected hydroxypyruvate and an aldehyde offers access to valuable polyhydroxy-α-keto acids. However, this undescribed aldolisation is highly challenging, especially regarding stereoselectivity. This reaction was explored using, as biocatalysts, a collection of aldolases selected from biodiversity. Several enzymes that belong to the same pyruvate aldolase Pfam family (PF03328) were found to produce the desired hexulosonic acids from hydroxypyruvate and d-glyceraldehyde with complementary stereoselectivities. One of them was selected for the proof of concept as a biocatalytic tool to prepare five (3S,4S) aldol adducts through an eco-friendly process.

Reactivity of thermally treated α-dicarbonyl compounds

The degradation reaction of thermally treated 3-deoxy-d-erythro-hexos-2- ulose and methylglyoxal, both key intermediates in Maillard chemistry, was investigated. Different analytical strategies were accomplished to cover the broad range of formed products and their different chemical behavior. These involved HPLC-DAD and accordingly LC/MS analysis of the quinoxaline derivates, GC/MS analysis of the acetylated quinoxalines, and GC-FID analysis of the decyl ester of acetic acid. As a main degradation product of 3-deoxy-d-erythro-hexos- 2-ulose, 5-(hydroxymethyl)furfural could be identified. At alkaline pH values, 3-deoxy-d-erythro-hexos-2-ulose generated various acids but no colored products. In contrast, thermal treatment of methylglyoxal yielded high molecular weight, brownish products. A dimer of methylglyoxal, first precursor for aldol-based polymerization of methylglyoxal, could be clearly identified by GC/MS.