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n‐ π * and Other Atomic Level Interactions of Formamides with Nucleobases and Base Analogs in Water
Author(s) -
Karim Rezwana,
Cheng Xian,
Record M. Thomas
Publication year - 2018
Publication title -
the faseb journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.709
H-Index - 277
eISSN - 1530-6860
pISSN - 0892-6638
DOI - 10.1096/fasebj.2018.32.1_supplement.792.32
Subject(s) - nucleobase , formamides , formamide , amide , chemistry , ring (chemistry) , stereochemistry , computational chemistry , dna , organic chemistry , biochemistry
To understand the molecular origins of favorable amide‐nucleobase interactions and predict or interpret effects of amides on nucleic acid processes, we quantify the preferential interactions of formamide and N‐methylated formamides with nucleobases and base analogs differing in amount and composition of water‐accessible surface area (ASA) by solubility assays. These formamide series solutes have much larger amide sp 2 C ASA than the alkylurea solutes studied previously. Using an established additive, ASA‐based analysis, we interpret these thermodynamic results to determine intrinsic strengths of interaction of each amide with unit area of the five types of nucleobase unified atoms (sp 2 C, sp 3 C; sp 2 N, sp 3 N; sp 2 O). All formamides interact favorably with all nucleobases and base analogs studied. “One‐way” analysis of results to date indicate favorable interactions of these formamides with all five types of unified atoms of nucleobases, and set the stage for a “two‐way” atom‐atom analysis quantifying interactions of the four atoms of amides (aliphatic sp 3 C; amide sp 2 C, sp 2 N and sp 2 O) with five atoms on nucleobase (aromatic ring sp 2 C and sp 2 N, methyl sp 3 C, amino sp 3 N, carbonyl sp 2 O). In particular, this “two‐way” analysis will quantify the favorable n‐π* interactions of nucleobase carbonyl O with amide sp 2 C and of formamide sp 2 O with nucleobase heterocyclic ring sp 2 C to compare with the very favorable n‐π* interactions of amide sp 2 O with homocyclic aromatic ring sp 2 C reported previously. Progress toward these goals will be reported. This abstract is from the Experimental Biology 2018 Meeting. There is no full text article associated with this abstract published in The FASEB Journal .