70147-59-0

Basic information

• Product Name: 1-(6-amino-purin-9-yl)-5-chloro-β-D-1,5-dideoxy-xylofuranose
• Synonyms: 1-(6-amino-purin-9-yl)-5-chloro-β-D-1,5-dideoxy-xylofuranose
• CAS NO: 70147-59-0
• Molecular Weight: 285.69
• Mol File: 70147-59-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1-(6-amino-purin-9-yl)-5-chloro-β-D-1,5-dideoxy-xylofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(6-amino-purin-9-yl)-5-chloro-β-D-1,5-dideoxy-xylofuranose(70147-59-0)
• EPA Substance Registry System: 1-(6-amino-purin-9-yl)-5-chloro-β-D-1,5-dideoxy-xylofuranose(70147-59-0)

Safety Data

• Hazardous Substances Data: 70147-59-0(Hazardous Substances Data)

Upstream product

• 42927-46-8 tetra-O-acetyl-D-xylofuranose 
• 66224-66-6 adenine 
• 15830-77-0 O²,O³,O⁵-triacetyl-1-(6-amino-purin-9-yl)-β-D-1-deoxy-xylofuranose 
• 524-69-6 adenine xyloside 

Downstream Products

• 203584-08-1 2'-O-acetyl-3'-deoxy-3'-fluoro-5'-S-(4-methoxyphenyl)-5'-thioadenosine 
• 203584-05-8 3'-deoxy-3'-fluoro-5'-S-(4-methoxyphenyl)-5'-thioadenosine 
• 203584-03-6 (2R,3R,4R,5S)-2-(6-Amino-purin-9-yl)-5-(4-methoxy-phenylsulfanylmethyl)-tetrahydro-furan-3,4-diol 

Relevant articles and documents

Nucleic acid related compounds. 101. S-adenosyl-L-homocysteine hydrolase does not hydrate (5'-fluoro)vinyl or (6'-halo)homovinyl analogues derived from 3'-deoxyadenosine or 3'-(chloro or fluoro)-3'-deoxyadenosine

S-Adenosyl-L-homocysteine (AdoHcy) hydrolase is crucial for the maintenance of biomethylation. The usual mechanistic sequence involves oxidation of AdoHcy at C3' followed by elimination of L-homocysteine, Michael addition of water, and reduction to give adenosine. A 6'- fluorohomovinyladenosine analogue (EDDFHA) undergoes hydration of the 5',6' double bond (hydrolytic activity) at a more rapid rate than oxidation at C3'. Three 4',5'-didehydro-5'-deoxy-5'-fluoro nucleoside analogues were prepared from 3'-deoxy- and 3'-(chloro and flouro)-3'-deoxyadenosine via generation of the vinyl fluorides by thermolysis of 5'-fluoro-5'-thioether sulfoxides. The 3'-deoxy analogues of 6'-halohomovinyladenosines were prepared by Wittig extension with a 3'-deoxy-5'-carboxaldehyde and halodestannylation of vinyl stannanes. The 3'-hydroxyl group appears to be essential for binding to AdoHcy hydrolase. No hydrolytic activity at C5', or C6' was observed with the nonoxidizable 3'-deoxy or 3'-(chloro or fluoro) analogues in contrast with their 3'-hydroxy counterparts (ZDDFA and EDDFHA). These 3'-modified analogues cannot reduce enzyme-bound NAD+ to NADH and do not produce time-dependent inhibition for AdoHcy hydrolase, but are weak competitive inhibitors (K(i) = 150-200 μM).