[5-(Adenin-9-yl)-5-deoxypentofuranosyl]phosphonates - A Novel Type of Nucleotide Analogs Related to HPMPA. I. Derivatives with L-arabino, D-arabino, 2-Deoxy-L-erythro and 2-Deoxy-L-threo Configuration

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Title:[5-(Adenin-9-yl)-5-deoxypentofuranosyl]phosphonates - A Novel Type of Nucleotide Analogs Related to HPMPA. I. Derivatives with L-arabino, D-arabino, 2-Deoxy-L-erythro and 2-Deoxy-L-threo Configuration
Creators:
Otmar, Miroslav
Rosenberg, Ivan
Masojídková, Milena
Holý, Antonín
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 58, 9, pp. 2159-2179

Abstract

[5-(Adenin-9-yl)-5-deoxypentofuranosyl]phosphonates, a new type of nucleotide analogs with fixed HPMPA structure, have been prepared. The synthesis of compounds of L-<i>arabino</i> (<i>IIa, IIb</i>), D-<i>arabino</i>(<i>XIVa, XIVb</i>), 2-deoxy-L-<i>erythro</i>(<i>IIIa, IIIb</i>) and 2-deoxy-L-<i>threo</i>(<i>IVa, IVb</i>) configuration is based on the Michelis-Arbuzov reaction of the fully protected methyl glycosides with triethyl phosphite and trimethylsilyl triflate which leads to anomeric mixture of diethyl (L-pentofuranosyl) phosphonates. The protected 5-<i>O</i>-tosyl derivatives react with sodium salt of adenine to give N<sup>9</sup>-substituted products which after total deprotection afforded the tittle nucleotide analogs. The fixation of the partial structure of HPMPA to form five-membered ring leads to a significant decrease, or a total loss, of biological activity.

Title:[5-(Adenin-9-yl)-5-deoxypentofuranosyl]phosphonates - A Novel Type of Nucleotide Analogs Related to HPMPA. I. Derivatives with L-arabino, D-arabino, 2-Deoxy-L-erythro and 2-Deoxy-L-threo Configuration
Creators:
Otmar, Miroslav
Rosenberg, Ivan
Masojídková, Milena
Holý, Antonín
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:58
Number:9
Page Range:pp. 2159-2179
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19932159UNSPECIFIED
ID Code:336
Item Type:Article
Deposited On:06 Feb 2009 17:00
Last Modified:06 Feb 2009 16:00

Citation

Otmar, Miroslav; Rosenberg, Ivan; Masojídková, Milena; Holý, Antonín (1993) [5-(Adenin-9-yl)-5-deoxypentofuranosyl]phosphonates - A Novel Type of Nucleotide Analogs Related to HPMPA. I. Derivatives with L-arabino, D-arabino, 2-Deoxy-L-erythro and 2-Deoxy-L-threo Configuration. Collection of Czechoslovak Chemical Communications, 58 (9). pp. 2159-2179. ISSN 0010-0765

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