PMID- 16716332
OWN - NLM
STAT- MEDLINE
DCOM- 20060925
LR  - 20090115
IS  - 0021-9673 (Print)
IS  - 0021-9673 (Linking)
VI  - 1121
IP  - 1
DP  - 2006 Jul 14
TI  - The role of molecular interaction fields on enantioselective and nonselective 
      separation of chiral sulfoxides.
PG  - 64-75
AB  - The separation of a series of 23 asymmetric sulfoxides, including the three 
      proton pump inhibitors (PPI) omeprazole, lansoprazole and pantoprazole was 
      investigated by HPLC, under reversed-phase elution with amylose 
      tris(3,5-dimethylphenylcarbamate), amylose tris[(S)-1-phenylethylcarbamate] and 
      amylose tris(3,5-dimethoxyphenylcarbamate) chiral stationary phases, CSP1-3, 
      respectively. The whole set of sulfoxides showed better enantioselectivity and 
      enantioresolution on CSP1. However, the three PPI were enantioseparated only when 
      using CSP1 and CSP3. It was observed an improved enantioselectivity and 
      enantioresolution on CSP3. The mechanisms of retention were evaluated by 
      molecular interaction fields (MIF) generated via GRID force field, which yielded 
      the geometric reasons leading to the scenario outlined. The enantioselective and 
      nonselective interactions are discussed in terms of the reported selectivity. The 
      steric structural outline of the CSP nonselective interaction sites is of major 
      importance to deliver the sulfoxides to the chiral selective sites where the 
      enantioselective interactions take place.
FAU - Montanari, M L C
AU  - Montanari ML
AD  - Departamento de Quimica, Universidade Federal de Sao Carlos, P.O. Box 676, 
      13565-905 Sao Carlos/SP, Brazil.
FAU - Cass, Q B
AU  - Cass QB
FAU - Leitao, A
AU  - Leitao A
FAU - Andricopulo, A D
AU  - Andricopulo AD
FAU - Montanari, C A
AU  - Montanari CA
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
DEP - 20060522
PL  - Netherlands
TA  - J Chromatogr A
JT  - Journal of chromatography. A
JID - 9318488
RN  - 0 (Sulfoxides)
SB  - IM
MH  - Models, Molecular
MH  - Molecular Structure
MH  - Stereoisomerism
MH  - Sulfoxides/*isolation & purification
EDAT- 2006/05/24 09:00
MHDA- 2006/09/26 09:00
CRDT- 2006/05/24 09:00
PHST- 2005/11/18 00:00 [received]
PHST- 2006/03/30 00:00 [revised]
PHST- 2006/04/05 00:00 [accepted]
PHST- 2006/05/24 09:00 [pubmed]
PHST- 2006/09/26 09:00 [medline]
PHST- 2006/05/24 09:00 [entrez]
AID - S0021-9673(06)00760-6 [pii]
AID - 10.1016/j.chroma.2006.04.072 [doi]
PST - ppublish
SO  - J Chromatogr A. 2006 Jul 14;1121(1):64-75. doi: 10.1016/j.chroma.2006.04.072. 
      Epub 2006 May 22.