Journal article
Synthesis of Acyclic Nucleoside and Nucleotide Analogues from Amino Acids: A Convenient Approach to a PMEA–PMPA Hybrid
Tetrahedron, Vol.56(29), pp.5077-5083
2000
DOI: 10.1016/S0040-4020(00)00422-1
Abstract
Nonracemic amino alcohols derived from common amino acids have been used to assemble acyclic nucleoside and nucleotide analogues with control of absolute stereochemistry. Both ( R)- and ( S)-2-amino-1-propanol, readily available from d- or l-alanine, were used to prepare the nucleoside analogues ( R)- and ( S)-9-[1-methyl-2-hydroxyethyl]adenine, and then the nucleotide analogues ( R)- and ( S)-9-[1-methyl-2-phosphonomethoxyethyl]adenine. In a similar fashion, the CBz derivative of l-threonine was used to prepare first (1 R,2 R)-9-[1-hydroxymethyl-2-hydroxypropyl]adenine, and then the bis phosphonomethoxy derivative. The bis phosphonate derived from threonine represents a unique structural hybrid of PMEA and PMPA, both of which have well established antiviral activity.
Details
- Title: Subtitle
- Synthesis of Acyclic Nucleoside and Nucleotide Analogues from Amino Acids: A Convenient Approach to a PMEA–PMPA Hybrid
- Creators
- Arlen L JefferyJae-Hun KimDavid F Wiemer
- Resource Type
- Journal article
- Publication Details
- Tetrahedron, Vol.56(29), pp.5077-5083
- Publisher
- Elsevier Ltd
- DOI
- 10.1016/S0040-4020(00)00422-1
- ISSN
- 0040-4020
- eISSN
- 1464-5416
- Language
- English
- Date published
- 2000
- Academic Unit
- Chemistry; Neuroscience and Pharmacology
- Record Identifier
- 9983985816702771
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