MilliporeSigma
  • From formamide to purine: an energetically viable mechanistic reaction pathway.

From formamide to purine: an energetically viable mechanistic reaction pathway.

The journal of physical chemistry. B (2013-01-26)
Jing Wang, Jiande Gu, Minh Tho Nguyen, Greg Springsteen, Jerzy Leszczynski
ABSTRACT

A step-by-step mechanistic pathway following the transformation of formamide to purine through a five-membered ring intermediate has been explored by density functional theory computations. The highlight of the mechanistic route detailed here is that the proposed pathway represents the simplest reaction pathway. All necessary reactants are generated from a single starting compound, formamide, through energetically viable reactions. Several important reaction steps are involved in this mechanistic route: formylation-dehydration, Leuckart reduction, five- and six-membered ring-closure, and deamination. On the basis of the study of noncatalytic pathways, catalytic water has been found to provide energetically viable step-by-step mechanistic pathways. Among these reaction steps, five-member ring-closure is the rate-determining step. The energy barrier (ca. 42 kcal/mol) of this rate-control step is somewhat lower than the rate-determining step (ca. 44 kcal/mol) for a pyrimidine-based pathway reported previously. The mechanistic pathway reported herein is less energetically demanding than for previously proposed routes to adenine.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Purine, 98%
Sigma-Aldrich
Formamide, ≥99.5% (GC), BioReagent, for molecular biology
Sigma-Aldrich
Formamide, ACS reagent, ≥99.5%
Sigma-Aldrich
Formamide, BioUltra, for molecular biology, ≥99.5% (T)
Sigma-Aldrich
Formamide, ReagentPlus®, ≥99.0% (GC)
Sigma-Aldrich
Formamide, spectrophotometric grade, ≥99%