Synthesis and stability studies of 2',3',5'-tri-O-acetyl-2-amino(-N6-cyclopentyl)-1-deazaadenosines

Sauro Vittori; Ram Chandra Mishra; Diego Dal Ben; Dhuldeo Kachare; Catia Lambertucci; Rosaria Volpini; Gloria Cristalli

doi:10.1080/15257770701542231

Synthesis and stability studies of 2',3',5'-tri-O-acetyl-2-amino(-N6-cyclopentyl)-1-deazaadenosines

Nucleosides Nucleotides Nucleic Acids. 2007;26(10-12):1439-42. doi: 10.1080/15257770701542231.

Authors

Sauro Vittori¹, Ram Chandra Mishra, Diego Dal Ben, Dhuldeo Kachare, Catia Lambertucci, Rosaria Volpini, Gloria Cristalli

Affiliation

¹ Dipartimento di Scienze Chimiche, Università di Camerino, I-62032 Camerino, MC, Italy. [email protected]

PMID: 18066801
DOI: 10.1080/15257770701542231

Abstract

In this article, we report on the synthesis of 2',3',5'-tri-O-acetyl-2-amino-1-deazaadenosine and of 2',3',5'-tri-O-acetyl-2-amino-N(6)-cyclopentyl-1-deazaadenosine, which are very versatile intermediates for the preparation of 2-substituted 1-deazaadenosine derivatives. The two synthesized compounds showed to be quite unstable, with the N(6)-substituted derivatives being less stable than the N(6)-unsubstituted counterpart, according to the calculated HOMO-LUMO energy gap. Stability studies were performed through HPLC-MS analysis.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Adenosine / analogs & derivatives*
Uridine / analogs & derivatives*
Uridine / chemical synthesis
Uridine / chemistry

Substances

2'-deoxy-2'-C-(thymine-1-ylmethyl)uridine
Adenosine
Uridine