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Structure Elucidation and Theoretical Investigation of Key Steps in the Biogenetic Pathway of Schisanartane Nortriterpenoids by Using DFT Methods
Author(s) -
Xiao WeiLie,
Lei Chun,
Ren Jie,
Liao TouGen,
Pu JianXin,
Pittman Charles U.,
Lu Yang,
Zheng YongTang,
Zhu HuaJie,
Sun HanDong
Publication year - 2008
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200801092
Subject(s) - computational chemistry , chemistry , density functional theory , stereochemistry
Rubrifloradilactone C ( 4 ), a novel bioactive nortriterpenoid, along with four other nortriterpenoids ( 1 – 3 , 5 ) were isolated from Schisandra rubriflora . The structure of 4 was determined by extensive NMR spectral analysis, computational evidence by using the GIAO method at the B3LYP/6–311++G(2d,p)//B3LYP/6–31G(d) levels, and X‐ray analysis. DFT at the B3LYP/6–311+G(d,p) level was selected to clarify the key mechanistic steps in the formation of 1 and 4 through transition‐state (TS) investigations. The effect of enzymes on the TS barriers was considered by using the polarized continuum model. Other possible products based on the new mechanism were predicted.