26207-44-3

Basic information

• Product Name: α-dapiofuranosyl-1,2-cyclic phosphate
• CAS NO: 26207-44-3
• Molecular Weight: 212.096
• Mol File: 26207-44-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: α-dapiofuranosyl-1,2-cyclic phosphate(CAS DataBase Reference)
• NIST Chemistry Reference: α-dapiofuranosyl-1,2-cyclic phosphate(26207-44-3)
• EPA Substance Registry System: α-dapiofuranosyl-1,2-cyclic phosphate(26207-44-3)

Safety Data

• Hazardous Substances Data: 26207-44-3(Hazardous Substances Data)

Upstream product

• 133-89-1 UDP-glucose 
• 2616-64-0 UDP-glucuronic acid 

Relevant articles and documents

Isotope Probing of the UDP-Apiose/UDP-Xylose Synthase Reaction: Evidence of a Mechanism via a Coupled Oxidation and Aldol Cleavage

The C-branched sugar d-apiose (Api) is essential for plant cell-wall development. An enzyme-catalyzed decarboxylation/pyranoside ring-contraction reaction leads from UDP-α-d-glucuronic acid (UDP-GlcA) to the Api precursor UDP-α-d-apiose (UDP-Api). We examined the mechanism of UDP-Api/UDP-α-d-xylose synthase (UAXS) with site-selectively2H-labeled and deoxygenated substrates. The analogue UDP-2-deoxy-GlcA, which prevents C-2/C-3 aldol cleavage as the plausible initiating step of pyranoside-to-furanoside conversion, did not give the corresponding Api product. Kinetic isotope effects (KIEs) support an UAXS mechanism in which substrate oxidation by enzyme-NAD+and retro-aldol sugar ring-opening occur coupled in a single rate-limiting step leading to decarboxylation. Rearrangement and ring-contracting aldol addition in an open-chain intermediate then give the UDP-Api aldehyde, which is intercepted via reduction by enzyme-NADH.