CAS:136522-35-5|(1S,4R)-4-Amino-2-cyclopentene-1-methanol

Catalogue Number:A603935
Chemical Name:(1S,4R)-4-Amino-2-cyclopentene-1-methanol
Synonyms:(1S-cis)-4-Amino-2-cyclopentene-1-methanol;
CAS Number:136522-35-5
Molecular Formula:C₆H₁₁NO
Appearance:No data available
Melting Point:No data available
Molecular Weight:113.16
Solubility:No data available
Category:Building Blocks; Miscellaneous;
Applications:(1S,4R)-4-Amino-2-cyclopentene-1-methanol is a reagent for preparing cyclic ADP-carbocyclic-ribose analogs via Yoshikawa’s phosphorylation and cyclocondensation (1). (1S,4R)-4-Amino-2-cyclopentene-1-methanol is also an intermediate for the synthesis of Abacavir (A105000). Abacavir is a carbocyclic 2′-deoxyguanosine nucleoside reverse transcriptase inhibitor and an anti-HIV drug used to treat HIV infection (2). Intracellular enzymes convert Abacavir to its active form, carbovir-triphosphate (CBV-TP), which then selectively inhibits HIV reverse transcriptase by incorporating into viral DNA (3). Abacavir is metabolized in the liver by uridine diphosphate glucuronyltransferase and alcohol dehydrogenase resulting in inactive glucuronide and carboxylate metabolites, respectively.
References:(1) Kudoh, T., et al.: Nucleosides Nucleotides Nucleic Acids 24, 655 (2005)
(2) Jackson, A., et al.: Antivir Ther. 17, 19 (2012)
(3) Yuen, G. J., et al.: Clin Pharmacokinet. 47, 351 (2008)
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