Structural determination of molecular stereochemistry using VCD spectroscopy and a conformational code: Absolute configuration and solution conformation of a chiral liquid pesticide, (R)-(1)-malathion

Chirality

Volumn 21, Issue 1 E, 2009, Pages

  Izumi, Hiroshi ^a   Ogata, Atsushi ^a   Nafie, Laurence A ^b,c   Dukor, Rina K ^c  

^a NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

^b SYRACUSE UNIVERSITY   (United States)

^c BIOTOOLS INC   (United States)

Author keywords

Absolute configuration; Conformation; Conformational code; Conformome; DFT calculation; Malathion; MM calculation; VCD spectroscopy

Indexed keywords

MALATHION; PESTICIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CIRCULAR DICHROISM; CONFORMATION; INFRARED SPECTROPHOTOMETRY; SOLUTION AND SOLUBILITY; STEREOISOMERISM; THERMODYNAMICS; VIBRATION;

CIRCULAR DICHROISM; MALATHION; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PESTICIDES; PHARMACEUTICAL SOLUTIONS; SPECTROPHOTOMETRY, INFRARED; STEREOISOMERISM; THERMODYNAMICS; VIBRATION;

EID: 77952998441     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20793     Document Type: Conference Paper

References (28)

1. Berkman CE, Thompson CM, Perrin SR. Synthesis, absolute-configuration, and analysis of malathion, malaoxon, and isomalathion enantiomers. Chem Res Toxicol 1993;6:718-723.
2. US EPA. Malathion for mosquito control. Available at: http://www.epa.gov/opp00001/health/mosquitoes/malathion4mosquitoes. htm#malathion.
3. Garcia-Reyes JF, Gilbert-Lopez B, Molina-Diaz A, Fernandez-Alba AR. Determination of pesticide residues in fruit-based soft drinks. Anal Chem 2008;80:8966-8974.
4. Garcia-Reyes JF, Jackson AU, Molina-Diaz A, Cooks RG. Desorption electrospray ionization mass spectrometry for trace analysis of agrochemicals in food. Anal Chem 2009;81:820-829.
5. Wang P, Jiang S, Liu D, Zhang H, Zhou Z. Enantiomeric resolution of chiral pesticides by high-performance liquid chromatography. J Agric Food Chem 2006;54:1577-1583.
6. Izumi H, Futamura S, Nafie LA, Dukor RK. Determination of molecular stereochemistry using vibrational circular dichroism spectroscopy: Absolute configuration and solution conformation of 5- formyl-cis, cis-1, 3, 5-trimethyl-3-hydroxymethylcyclohexane-1-carboxylic acid lactone. Chem Rec 2003;3:112-119.
7. Izumi H, Yamagami S, Futamura S, Nafie LA, Dukor RK. Direct observation of odd-even effect for chiral alkyl alcohols in solution using vibrational circular dichroism spectroscopy. J Am Chem Soc 2004;126: 194-198.
8. Izumi H, Futamura S, Tokita N, Hamada Y. Fliplike motion in the thalidomide dimer: conformational analysis of (R)-thalidomide using vibrational circular dichroism spectroscopy. J Org Chem 2007;72:277-279.
9. Izumi H, Ogata A, Nafie LA, Dukor RK. Vibrational circular dichroism analysis reveals a conformational change of the baccatin III ring of paclitaxel: visualization of conformations using a new code for structure- activity relationships. J Org Chem 2008;73:2367-2372.
10. Izumi H, Ogata A, Nafie LA, Dukor RK. A revised conformational code for the exhaustive analysis of conformers with one-to-one correspondence between conformation and code: Application to the VCD analysis of (S)-ibuprofen. J Org Chem 2009;74:1231-1236.
11. Monde K, Taniguchi T, Miura N, Vairappan CS, Suzuki M. Absolute configurations of endoperoxides determined by vibrational circular dichroism (VCD). Tetrahedron Lett 2006;47:4389-4392.
12. Monde K, Taniguchi T, Miura N, Nishimura SI. Specific band observed in VCD predicts the anomeric configuration of carbohydrates. J Am Chem Soc 2004;126:9496-9497.
13. Zhao C, Polavarapu PL, Grosenick H, Schurig V. Vibrational circular dichroism, absolute configuration and predominant conformations of volatile anesthetics: enflurane. J Mol Struct 2000;550:105-115.
14. Wang F, Polavarapu PL, Drabowicz J, Mikolajczyk M. Absolute configurations, predominant conformations and tautomeric structures of enantiomeric tert-butylphenylphosphine oxides. J Org Chem 2000; 65:7561-7565.
15. Wang F, Polavarapu PL. Vibrational circular dichroism: predominant conformations and intermolecular interactions in (R)-2-butanol. J Phys Chem A 2000;104:10683-10687.
16. Drabowicz J, Dudzinski B, Mikolajczyk M, Wang F, Dehlavi A, Goring J, Park M, Rizzo CJ, Polavarapu PL, Biscarini P, Wieczorek MW, Majzner WR. Absolute configuration, predominant conformations, and vibrational circular dichroism spectra of enantiomers of n-butyl tertbutyl sulfoxide. J Org Chem 2001;66:1122-1129.
17. Wang F, Wang H, Polavarapu PL, Rizzo CJ. Absolute configuration and conformational stability of (1)-2, 5-dimethylthiolane and-2, 5- dimethylsulfolane. J Org Chem 2001;66:3507-3512.
18. Wang F, Polavarapu PL. Predominant conformations of (2R, 3R) -2, 3- butanediol. J Phys Chem A 2001;105:6991-6997.
19. Wang F, Polavarapu PL, Drabowicz J, Mikolajczyk M, Lyzwa P. Absolute configurations, predominant conformations, and tautomeric structures of enantiomeric tert-butylphenylphosphinothioic acid. J Org Chem 2001;66:9015-9019.
20. Wang F, Polavarapu PL, Lebon F, Longhi G, Abbate S, Catellani M. Absolute configuration and conformational stability of (S)-(1)-3-(2- methylbutyl)thiophene and (1)-3, 4-di[(S)-2-methylbutyl)]thiophene and their polymers. J Phys Chem A 2002;106:5918-5923.
21. Wang F, Polavarapu PL, Schurig V, Schmidt R. Absolute configuration and conformational analysis of a degradation product of inhalation anesthetic sevoflurane: A vibrational circular dichroism study. Chirality 2002;14:618-624.
22. Polavarapu PL. The absolute configuration of bromochlorofluoromethane. Angew Chem Int Ed 2002;41:4544-4546.
23. Wang F, Wang Y, Polavarapu PL, Li TY, Drabowicz J, Pietrusiewicz KM, Zygo K. Absolute configuration of tert-butyl-1-(2-methylnaphthyl)- phosphine oxide. J Org Chem 2002;67:6539-6541.
24. Wang F, Polavarapu PL, Lebon F, Longhi G, Abbate S, Catellani M. Conformational analysis of (S)-(1)-1-bromo-2-methylbutane and the influence of bromine on conformational stability. J Phys Chem A 2002;106:12365-12369.
25. Mugishima T, Tsuda M, Kasai Y, Ishiyama H, Fukushi E, Kawabata J, Watanabe M, Akao K, Kobayashi J. Absolute stereochemistry of citrinadins A and B from marine-derived fungus. J Org Chem 2005;70: 9430-9435.
26. Cichewicz RH, Clifford LJ, Lassen PR, Cao XL, Freedman TB, Nafie LA, Deschamps JD, Kenyon VA, Flanary JR, Holman TR, Crews P. Stereochemical determination and bioactivity assessment of (S)-(1)- curcuphenol dimers isolated from the marine sponge Didiscus aceratus and synthesized through laccase biocatalysis. Bioorg Med Chem 2005;13:5600-5612.
27. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA. Gaussian 03. Wallingford CT: Gaussian Inc; 2004.
28. Frisch MJ, Trucks GW, Cheeseman JB. Systematic model chemistries based on DFT theory: comparison with traditional models and with experiment. In: Seminario JM, editor. Recent developments and applications of modern density functional theory, Vol. 4. Amsterdam: Elsevier; 1996.