Measurement of long range H, C couplings in natural products in orienting media: A tool for structure elucidation of natural products

Journal of Magnetic Resonance

Volumn 163, Issue 2, 2003, Pages 353-359

  Verdier, Laurent ^a   Sakhaii, Peyman ^a   Zweckstetter, Markus ^a   Griesinger, Christian ^a  

^a MAX PLANCK INSTITUTE FOR BIOPHYSICAL CHEMISTRY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; CONFORMATIONS; MOLECULAR ORIENTATION; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC SOLVENTS; SOLUBILITY; STEREOCHEMISTRY;

DIPOLAR COUPLINGS;

MOLECULAR PHYSICS;

HOMO;

CARBON; DRUG DERIVATIVE; HYDROGEN; MENTHOL; POLY GAMMA BENZYL GLUTAMATE; POLY-GAMMA-BENZYL-L-GLUTAMATE; POLYGLUTAMIC ACID;

ARTICLE; CHEMISTRY; COMPARATIVE STUDY; CONFORMATION; CRYSTALLIZATION; CRYSTALLOGRAPHY; EVALUATION; HYDROGEN BOND; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE; REPRODUCIBILITY; SENSITIVITY AND SPECIFICITY; SOLUBILITY; SOLUTION AND SOLUBILITY; VALIDATION STUDY;

CARBON; CRYSTALLIZATION; CRYSTALLOGRAPHY; HYDROGEN; HYDROGEN BONDING; MENTHOL; MOLECULAR CONFORMATION; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; POLYGLUTAMIC ACID; REPRODUCIBILITY OF RESULTS; SENSITIVITY AND SPECIFICITY; SOLUBILITY; SOLUTIONS;

EID: 0042029732     PISSN: 10907807     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1090-7807(03)00063-6     Document Type: Article

References (25)

1. Canet I., Lovschall J., Courtieu J. Liq. Cryst. 16:1994;405 Meddour A., Berdague P., Hedli A., Courtieu J., Lesot P. J. Am. Chem. Soc. 119:1997;4502 Merlet D., Ancian B., Courtieu J., Lesot P. J. Am. Chem. Soc. 121:1999;5249.
2. Canet I., Lovschall J., Courtieu J. Liq. Cryst. 16:1994;405 Meddour A., Berdague P., Hedli A., Courtieu J., Lesot P. J. Am. Chem. Soc. 119:1997;4502 Merlet D., Ancian B., Courtieu J., Lesot P. J. Am. Chem. Soc. 121:1999;5249.
3. Canet I., Lovschall J., Courtieu J. Liq. Cryst. 16:1994;405 Meddour A., Berdague P., Hedli A., Courtieu J., Lesot P. J. Am. Chem. Soc. 119:1997;4502 Merlet D., Ancian B., Courtieu J., Lesot P. J. Am. Chem. Soc. 121:1999;5249.
4. Sarfati M., Lesot P., Merlet D., Courtieu J. Chem. Commun. 21:2000;2069.
5. Sandstrom D., Summanen K.T., Levitt M.H. J. Am. Chem. Soc. 116:1994;9357 Sandstrom D., Levitt M.H. J. Am. Chem. Soc. 118:1996;6966.
6. Sandstrom D., Summanen K.T., Levitt M.H. J. Am. Chem. Soc. 116:1994;9357 Sandstrom D., Levitt M.H. J. Am. Chem. Soc. 118:1996;6966.
7. Emsley L.W., Lindon J.C. NMR spectroscopy using Liquid Crystal Solvents. 1975;Pergamon Press, Oxford.
8. Thiele C., Berger S. Org. Lett. 5:2003;705.
9. Ramirez B.E., Bax A. J. Am. Chem. Soc. 120:1998;9106 Cai M., Huang Y., Zheng R., Wei S.-Q., Ghirlando R., Lee M.S., Craigie R., Gronenborn A.M., Clore G.M. Nat. Struct. Biol. 5:1998;903 Clore G.M., Gronenborn A.M. Proc. Natl. Acad. Sci. USA. 95:1998;5891 Tian F., Fowler C.A., Zartler E.R., Jenney F.A. Jr., Adams M.W., Prestegard J.H. J. Biomol. NMR. 18:2000;23 Delaglio F., Kontaxis G., Bax A. J. Am. Chem. Soc. 122:2000;2142 Zweckstetter M., Bax A. J. Am. Chem. Soc. 123:2001;9490 Prestegard J.H., Kishore A.I. Curr. Opin. Chem. Biol. 5:2001;584 Prestegard J.H., Valafar H., Glushka J., Tian F. Biochemistry. 40:2001;8677 Fowler C.A., Tian F., Al-Hashimi H.M., Prestegard J.H. J. Mol. Biol. 304:2000;447.
10. Ramirez B.E., Bax A. J. Am. Chem. Soc. 120:1998;9106 Cai M., Huang Y., Zheng R., Wei S.-Q., Ghirlando R., Lee M.S., Craigie R., Gronenborn A.M., Clore G.M. Nat. Struct. Biol. 5:1998;903 Clore G.M., Gronenborn A.M. Proc. Natl. Acad. Sci. USA. 95:1998;5891 Tian F., Fowler C.A., Zartler E.R., Jenney F.A. Jr., Adams M.W., Prestegard J.H. J. Biomol. NMR. 18:2000;23 Delaglio F., Kontaxis G., Bax A. J. Am. Chem. Soc. 122:2000;2142 Zweckstetter M., Bax A. J. Am. Chem. Soc. 123:2001;9490 Prestegard J.H., Kishore A.I. Curr. Opin. Chem. Biol. 5:2001;584 Prestegard J.H., Valafar H., Glushka J., Tian F. Biochemistry. 40:2001;8677 Fowler C.A., Tian F., Al-Hashimi H.M., Prestegard J.H. J. Mol. Biol. 304:2000;447.
11. Ramirez B.E., Bax A. J. Am. Chem. Soc. 120:1998;9106 Cai M., Huang Y., Zheng R., Wei S.-Q., Ghirlando R., Lee M.S., Craigie R., Gronenborn A.M., Clore G.M. Nat. Struct. Biol. 5:1998;903 Clore G.M., Gronenborn A.M. Proc. Natl. Acad. Sci. USA. 95:1998;5891 Tian F., Fowler C.A., Zartler E.R., Jenney F.A. Jr., Adams M.W., Prestegard J.H. J. Biomol. NMR. 18:2000;23 Delaglio F., Kontaxis G., Bax A. J. Am. Chem. Soc. 122:2000;2142 Zweckstetter M., Bax A. J. Am. Chem. Soc. 123:2001;9490 Prestegard J.H., Kishore A.I. Curr. Opin. Chem. Biol. 5:2001;584 Prestegard J.H., Valafar H., Glushka J., Tian F. Biochemistry. 40:2001;8677 Fowler C.A., Tian F., Al-Hashimi H.M., Prestegard J.H. J. Mol. Biol. 304:2000;447.
12. Ramirez B.E., Bax A. J. Am. Chem. Soc. 120:1998;9106 Cai M., Huang Y., Zheng R., Wei S.-Q., Ghirlando R., Lee M.S., Craigie R., Gronenborn A.M., Clore G.M. Nat. Struct. Biol. 5:1998;903 Clore G.M., Gronenborn A.M. Proc. Natl. Acad. Sci. USA. 95:1998;5891 Tian F., Fowler C.A., Zartler E.R., Jenney F.A. Jr., Adams M.W., Prestegard J.H. J. Biomol. NMR. 18:2000;23 Delaglio F., Kontaxis G., Bax A. J. Am. Chem. Soc. 122:2000;2142 Zweckstetter M., Bax A. J. Am. Chem. Soc. 123:2001;9490 Prestegard J.H., Kishore A.I. Curr. Opin. Chem. Biol. 5:2001;584 Prestegard J.H., Valafar H., Glushka J., Tian F. Biochemistry. 40:2001;8677 Fowler C.A., Tian F., Al-Hashimi H.M., Prestegard J.H. J. Mol. Biol. 304:2000;447.
13. Ramirez B.E., Bax A. J. Am. Chem. Soc. 120:1998;9106 Cai M., Huang Y., Zheng R., Wei S.-Q., Ghirlando R., Lee M.S., Craigie R., Gronenborn A.M., Clore G.M. Nat. Struct. Biol. 5:1998;903 Clore G.M., Gronenborn A.M. Proc. Natl. Acad. Sci. USA. 95:1998;5891 Tian F., Fowler C.A., Zartler E.R., Jenney F.A. Jr., Adams M.W., Prestegard J.H. J. Biomol. NMR. 18:2000;23 Delaglio F., Kontaxis G., Bax A. J. Am. Chem. Soc. 122:2000;2142 Zweckstetter M., Bax A. J. Am. Chem. Soc. 123:2001;9490 Prestegard J.H., Kishore A.I. Curr. Opin. Chem. Biol. 5:2001;584 Prestegard J.H., Valafar H., Glushka J., Tian F. Biochemistry. 40:2001;8677 Fowler C.A., Tian F., Al-Hashimi H.M., Prestegard J.H. J. Mol. Biol. 304:2000;447.
14. Ramirez B.E., Bax A. J. Am. Chem. Soc. 120:1998;9106 Cai M., Huang Y., Zheng R., Wei S.-Q., Ghirlando R., Lee M.S., Craigie R., Gronenborn A.M., Clore G.M. Nat. Struct. Biol. 5:1998;903 Clore G.M., Gronenborn A.M. Proc. Natl. Acad. Sci. USA. 95:1998;5891 Tian F., Fowler C.A., Zartler E.R., Jenney F.A. Jr., Adams M.W., Prestegard J.H. J. Biomol. NMR. 18:2000;23 Delaglio F., Kontaxis G., Bax A. J. Am. Chem. Soc. 122:2000;2142 Zweckstetter M., Bax A. J. Am. Chem. Soc. 123:2001;9490 Prestegard J.H., Kishore A.I. Curr. Opin. Chem. Biol. 5:2001;584 Prestegard J.H., Valafar H., Glushka J., Tian F. Biochemistry. 40:2001;8677 Fowler C.A., Tian F., Al-Hashimi H.M., Prestegard J.H. J. Mol. Biol. 304:2000;447.
15. Ramirez B.E., Bax A. J. Am. Chem. Soc. 120:1998;9106 Cai M., Huang Y., Zheng R., Wei S.-Q., Ghirlando R., Lee M.S., Craigie R., Gronenborn A.M., Clore G.M. Nat. Struct. Biol. 5:1998;903 Clore G.M., Gronenborn A.M. Proc. Natl. Acad. Sci. USA. 95:1998;5891 Tian F., Fowler C.A., Zartler E.R., Jenney F.A. Jr., Adams M.W., Prestegard J.H. J. Biomol. NMR. 18:2000;23 Delaglio F., Kontaxis G., Bax A. J. Am. Chem. Soc. 122:2000;2142 Zweckstetter M., Bax A. J. Am. Chem. Soc. 123:2001;9490 Prestegard J.H., Kishore A.I. Curr. Opin. Chem. Biol. 5:2001;584 Prestegard J.H., Valafar H., Glushka J., Tian F. Biochemistry. 40:2001;8677 Fowler C.A., Tian F., Al-Hashimi H.M., Prestegard J.H. J. Mol. Biol. 304:2000;447.
16. Ramirez B.E., Bax A. J. Am. Chem. Soc. 120:1998;9106 Cai M., Huang Y., Zheng R., Wei S.-Q., Ghirlando R., Lee M.S., Craigie R., Gronenborn A.M., Clore G.M. Nat. Struct. Biol. 5:1998;903 Clore G.M., Gronenborn A.M. Proc. Natl. Acad. Sci. USA. 95:1998;5891 Tian F., Fowler C.A., Zartler E.R., Jenney F.A. Jr., Adams M.W., Prestegard J.H. J. Biomol. NMR. 18:2000;23 Delaglio F., Kontaxis G., Bax A. J. Am. Chem. Soc. 122:2000;2142 Zweckstetter M., Bax A. J. Am. Chem. Soc. 123:2001;9490 Prestegard J.H., Kishore A.I. Curr. Opin. Chem. Biol. 5:2001;584 Prestegard J.H., Valafar H., Glushka J., Tian F. Biochemistry. 40:2001;8677 Fowler C.A., Tian F., Al-Hashimi H.M., Prestegard J.H. J. Mol. Biol. 304:2000;447.
17. Ramirez B.E., Bax A. J. Am. Chem. Soc. 120:1998;9106 Cai M., Huang Y., Zheng R., Wei S.-Q., Ghirlando R., Lee M.S., Craigie R., Gronenborn A.M., Clore G.M. Nat. Struct. Biol. 5:1998;903 Clore G.M., Gronenborn A.M. Proc. Natl. Acad. Sci. USA. 95:1998;5891 Tian F., Fowler C.A., Zartler E.R., Jenney F.A. Jr., Adams M.W., Prestegard J.H. J. Biomol. NMR. 18:2000;23 Delaglio F., Kontaxis G., Bax A. J. Am. Chem. Soc. 122:2000;2142 Zweckstetter M., Bax A. J. Am. Chem. Soc. 123:2001;9490 Prestegard J.H., Kishore A.I. Curr. Opin. Chem. Biol. 5:2001;584 Prestegard J.H., Valafar H., Glushka J., Tian F. Biochemistry. 40:2001;8677 Fowler C.A., Tian F., Al-Hashimi H.M., Prestegard J.H. J. Mol. Biol. 304:2000;447.
18. Meiler J., Prompers J., Peti W., Griesinger C., Brüschweiler R. J. Am. Chem. Soc. 123(25):2001;6098-6107 Peti W., Meiler J., Brüschweiler R., Griesinger C. J. Am. Chem. Soc. 124:2002;5822-5833 Tolman J.R., Al-Hashimi H.M., Kay L.E., Prestegard J.H. J. Am. Chem. Soc. 123:2001;1416-1424 Tolman J.R. J. Am. Chem. Soc. 124:2002;12020-12030.
19. Meiler J., Prompers J., Peti W., Griesinger C., Brüschweiler R. J. Am. Chem. Soc. 123(25):2001;6098-6107 Peti W., Meiler J., Brüschweiler R., Griesinger C. J. Am. Chem. Soc. 124:2002;5822-5833 Tolman J.R., Al-Hashimi H.M., Kay L.E., Prestegard J.H. J. Am. Chem. Soc. 123:2001;1416-1424 Tolman J.R. J. Am. Chem. Soc. 124:2002;12020-12030.
20. Meiler J., Prompers J., Peti W., Griesinger C., Brüschweiler R. J. Am. Chem. Soc. 123(25):2001;6098-6107 Peti W., Meiler J., Brüschweiler R., Griesinger C. J. Am. Chem. Soc. 124:2002;5822-5833 Tolman J.R., Al-Hashimi H.M., Kay L.E., Prestegard J.H. J. Am. Chem. Soc. 123:2001;1416-1424 Tolman J.R. J. Am. Chem. Soc. 124:2002;12020-12030.
21. Meiler J., Prompers J., Peti W., Griesinger C., Brüschweiler R. J. Am. Chem. Soc. 123(25):2001;6098-6107 Peti W., Meiler J., Brüschweiler R., Griesinger C. J. Am. Chem. Soc. 124:2002;5822-5833 Tolman J.R., Al-Hashimi H.M., Kay L.E., Prestegard J.H. J. Am. Chem. Soc. 123:2001;1416-1424 Tolman J.R. J. Am. Chem. Soc. 124:2002;12020-12030.
22. Bax A., Freeman R., Frenkiel T.A. J. Am. Chem. Soc. 103:1981;2102.
23. Richardson J.M., Titman J.J., Keeler J., Neuhaus D. J. Magn. Res. 93:1991;533.
24. Zweckstetter M., Bax A. J. Am. Chem. Soc. 122:2000;3791.
25. Losonczi J.A., Andrec M., Fischer M.W.F., Prestegard J.H. J. Magn. Res. 138:1999;334-342.