Theoretical aspects of the structural chemistry of biotin II. Carboxylated biotins

✍ Scribed by Gerald M. Maggiora

• Publisher: Elsevier Science
• Year: 1974
• Tongue: English
• Weight: 540 KB
• Volume: 43
• Category: Article
• ISSN: 0022-5193
• DOI: 10.1016/s0022-5193(74)80044-5

✦ Synopsis

All valence-electron self-consistent field molecular orbital calculations (CNDO/2) were performed on the enol form of biotin and several Ncarboxy and O-carboxybiotin molecules. The electronic aspects of biotin carboxylation and decarboxylation or CO2 transfer were investigated. Enhanced nucleophilic reactivity of the biotin-enol species was examined in the light of its overall effect on the rate of carboxylation. Comparative reactivities of N-carboxy and O-carboxybiotin were also examined in terms of the net atomic charges and overlap populations of the reactive groups.