Observation and characterization of a specific vibrational circular dichroism band in phenyl glycosides

Chirality

Volumn 20, Issue 3-4, 2008, Pages 446-453

  Taniguchi, Tohru ^a   Tone, Ikuko ^a   Monde, Kenji ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

Aromatic glycoside; Carbohydrate; Density functional theory; Glycoconjugate; Vibrational circular dichroism

Indexed keywords

CARBOHYDRATE; ELEUTHEROSIDE B1; GLYCOCONJUGATE; GLYCOSIDE; PHENYL 2 DEOXY 3,4 O ETHYLENE BETA DEXTRO THREO PENTOPYRANOSIDE; PHENYL 2 DEOXY ALPHA DEXTRO THREO PENTOPYRANOSIDE; PHENYL 2 DEOXY BETA DEXTRO THREO PENTOPYRANOSIDE; PHENYL 3,4 DI O ACETYL 2 DEOXY ALPHA DEXTRO THREO PENTOPYRANOSIDE; PHENYL 3,4 DI O ACETYL 2 DEOXY BETA DEXTRO THREO PENTOPYRANOSIDE; PHENYL GLYCOSIDE; SALICIN; UNCLASSIFIED DRUG; VANCOMYCIN;

ARTICLE; CIRCULAR DICHROISM; DENSITY FUNCTIONAL THEORY; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SOLVATION; STEREOCHEMISTRY;

EID: 39749115610     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20465     Document Type: Article

References (38)

1. 1 Dudley RJ, Mason SF, Peacock RD. Infrared vibrational circular dichroism. J Chem Soc Chem Commun 1972 ; 1084–1085.
2. 2 Hsu EC, Holzwarth G. Vibratinal circular dichroism observed in crystalline α‐NiSO 4 ·6H 2 O and α‐ZnSeO 4 ·6H 2 O between 1900 and 5000 cm −1. J Phys Chem 1973 ; 59: 4678–4685.
3. 3 Holzwarth G, Hsu EC, Mosher HS, Faulkner TR, Moscowitz A. Infrared circular dichroism of carbon‐hydrogen and carbon–detuterium stretching modes. J Am Chem Soc 1974 ; 96: 251–252.
4. 4 Stephens PJ, Devlin FJ. Determination of the structure of chiral molecules using ab initio vibrational circular dichroism spectroscopy. Chirality 2000 ; 12: 172–179.
5. 5 Polavarapu PL, He J. Chiral analysis using mid‐IR vibrational CD spectroscopy. Anal Chem 2004 ; 76: 61A–67A.
6. 6 Nafie LA, Dukor RK. Vibrational optical activity in chiral analysis. In: Busch KW, Busch MA, editors. Chiral analysis. Netherlands: Elsevier ; 2006. p 505–544.
7. 7 Keiderling TA. Peptide and protein conformational studies with vibrational circular dichroism and related spectroscopies. In: Berova N, Nakanishi K, Woody RW, editors. Circular dichroism: principles and applications. New York: Wiley‐VCH ; 2000. p 621–666.
8. 8 Lee KK, Hahn S, Oh KI, Choi JS, Joo C, Lee H, Han H, Cho M. Structure of N ‐acetylproline amide in liquid water: Experimentally measured and numerically simulated infrared and vibrational circular dichroism spectra. J Phys Chem B 2006 ; 110: 18834–18843.
9. 9 Turner DR, Kubelka J. Infrared and vibrational CD spectra of partially solvated a‐helices: DFT‐based simulations with explicit solvent. J Phys Chem B 2007 ; 111: 1834–1845.
10. 10 Annamalai A, Keiderling TA. Vibrational circular dichroism of poly (ribonucleic acids). A comparative study in aqueous solution. J Am Chem Soc 1987 ; 109: 3125–3132.
11. 11 Krummel AT, Zanni MT. Interpreting DNA vibrational circular dichroism spectra using a coupling model from two‐dimensional infrared spectroscopy. J Phys Chem B 2006 ; 110: 24720–24727.
12. 12 Marcott C, Havel HA, Overend J, Moscowitz A. Vibrational circular dichroism and individual chiral centers. An example from the sugars. J Am Chem Soc 1978 ; 100: 7088–7089.
13. 13 Paterlini MG, Freedman TB, Nafie LA. Ring current enhanced vibrational circular dichroism in the CH‐stretching motions of sugars. J Am Chem Soc 1986 ; 108: 1389–1397.
14. 14 Back DM, Polavarapu PL. Fourier‐transform infrared, vibrational circular dichroism of sugars. A spectra‐structure correlation. Carbohydr Res 1984 ; 133: 163–167.
15. 15 Taniguchi T, Monde K. Chiroptical analysis of glycoconjugates by vibrational circular dichroism (VCD). Trends Glycosci Glycotechnol 2007 ; 19: 149–166.
16. 16 Taniguchi T, Monde K. Spectra–Structures relationship on carbohydrate VCD and its application to glycoconjugates. Chem Asian (in press).
17. 17 Urbanova M, Pancoska P, Keiderling TA. Spectroscopic study of the temperature‐dependent conformation of glucoamylase. Biochim Biophys Acta 1993 ; 1203: 290–294.
18. 18 Shanmugan G. ; Polavarapu PL. Structures of intact glycoproteins from vibrational circular dichroism. Proteins 2006 ; 63: 768–776.
19. 19 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.
20. 20 Taniguchi T, Monde K, Miura N, Nishimura SI. A chracteristic CH band in VCD of methyl glycosidic carbohydrates. Tetrahedron Lett 2004 ; 45: 8451–8453.
21. 21 Taniguchi T, Monde K. Vibrational circular dichroism (VCD) studies on disaccharides in the CH region: toward discrimination of the glycosidic linkage position. Org Biomol Chem 2007 ; 5: 1104–1110.
22. 22 Lindhorst TK. Antitumor and antimicrobial glycoconjugates. In: Fraser‐Reid BO, Tatsuta K, Thiem J, editors. Glycoscience. Berlin: Springer ; 2001 p 2393–2439.
23. 23 Kren V. Chemical biology and biomedicine of glycosylated natural compounds. In: Fraser‐Reid BO, Tatsuta K, Thiem J, editors. Glycoscience. Berlin: Springer ; 2001. p 2471–2529.
24. 24 Jacobsson M, Malmberg J, Ellervik U. Aromatic O ‐glycosylation. Carbohydr Res 2006 ; 341: 1266–1281.
25. 25 Zhang C, Griffith BR, Fu Q, Albermann C, Fu X, Lee IK, Li L, Thorson JS. Exploiting the reversibility of natural product glycosyltransferase‐catalyzed reactions. Science 2006 ; 313: 1291–1294.
26. 26 Kondo T, Yoshida K, Nakagawa A, Kawai T, Tamura H, Goto T. Structural basis of blue‐colour development in flower petals from Commelica communis. Nature 1992 ; 358: 515–518.
27. 27 Jung JH, John G, Yoshida K, Shimizu T. Self‐assembling structures of long‐chain phenyl glucoside influenced by the introduction of double bonds. J Am Chem Soc 2002 ; 124: 10674–10675.
28. 28 Usuki T, Nakanishi K, Ellestad GA. Spin‐trapping of the p ‐benzyne intermediates from ten‐membered enediyne calicheamicin γ 1 I. Org Lett 2006 ; 8: 5461–5463.
29. 29 SPARTAN ′02. http://www.wavefun.com
30. 30 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, 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, Revision C.02. Wallingford, CT: Gaussian, Inc ; 2004.
31. 31 Freedman TB, Cao X, Dukor RK, Nafie LA. Absolute configuration determination of chiral molecules in the solution state using vibrational circular dichroism. Chirality 2003 ; 15: 743–758.
32. 32 Urbanová M, Setnicka V, Devlin FJ, Stephens PJ. Determination of molecular structure in solution using vibrational circular dichroism spectroscopy: The supramolecular tetramer of S‐2,2′‐dimethyl‐biphenyl‐6,6′‐dicarboxylic acid. J Am Chem Soc 2005 ; 127: 6700–6711.
33. 33 Monde K, Taniguchi T, Miura N, Vairappan CS, Suzuki M. Absolute configurations of brominated sesquiterpenes determined by vibrational circular dichroism. Chirality 2006 ; 18: 335–339.
34. 34 Brotin T, Cavagnat D, Dutasta JP, Buffeteau T. Vibrational circular dichroism study of optically pure cryptophane‐A. J Am Chem Soc 2006 ; 128: 5533–5540.
35. 35 Günzler H, Gremlich HU. IR spectroscopy–An introduction. (Blümich MJ, Transl.). Weinheim: Wiley‐VCH ; 2002. p 171–278.
36. 36 Socrates G. Infrared and raman characteristic group frequencies. Chichester: Wiley ; 2001. p 101–104.
37. 37 Silverstein RM, Webster FX. Spectrometric identification of organic compounds. New York: Wiley ; 1998. p 90–92.
38. 38 Bose PK, Polavarapu PL. Acetate groups as probes of the stereochemistry of carbohydrates: a vibrational circular dichroism study. Carbohydr Res 1999 ; 322: 135–141.