Key result
Raman spectroscopy reveals N1-protonated aqueous PMEA adopts a syn-like conformation unlike common AMPs.
Why the study?
The acid-base and structural properties of the antiviral nucleotide analogue PMEA in aqueous solutions and their differences from common AMP counterparts were not fully characterized.
Raman spectroscopy reveals that N1-protonated PMEA adopts a "syn-like" conformation in aqueous solution, unlike its crystalline form or common AMPs, due to adenine protonation and group flexibility.
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Does not alter clinical use of nucleotide analogs; leaves open conformational effects on PMEA activity in vivo.
Kopecký et al. (2002) studied this question. 9-[2-(phosphonomethoxy)ethyl]adenine (PMEA) in aqueous solutions vs. adenosine monophosphate counterparts (5'-AMP, 3'-AMP, and 2'-AMP) was evaluated on Acid-base and structural properties (spectroscopic pKa values, sites of protonation, abundance). Raman spectroscopy revealed a 'syn-like' conformation for N1-protonated PMEA species in aqueous solutions, differing from the 'anti-like' conformation of crystalline H2PMEA or common AMPs.
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