Unpredictable stereochemical preferences for mu opioid receptor activity in an exhaustively stereodiversified library of 1,4-enediols

Organic Letters

Volumn 5, Issue 5, 2003, Pages 633-636

  Shi, Zhangjie ^a   Harrison, Bryce A ^a   Verdine, Gregory L ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ENDOMORPHIN 1; ENDORPHIN DERIVATIVE; ENKEPHALIN[2 DEXTRO ALANINE 4 METHYLPHENYLALANINE 5 GLYCINE]; GUANINE NUCLEOTIDE BINDING PROTEIN; MU OPIATE RECEPTOR; N METHYL N [7 (1 PYRROLIDINYL) 1 OXASPIRO[4.5]DEC 8 YL]BENZENEACETAMIDE; TRITIUM; ALCOHOL DERIVATIVE; GUANOSINE 5' O (3 THIOTRIPHOSPHATE); SULFUR;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; CROSS LINKING; DRUG EFFICACY; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; DRUG SYNTHESIS; EMBRYO; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; NONHUMAN; PHARMACOPHORE; RADIOASSAY; STEREOCHEMISTRY; STEREOISOMERISM; TRANS ISOMER; ANIMAL; BINDING COMPETITION; CHEMISTRY; CHO CELL; COMBINATORIAL CHEMISTRY; ENZYME SPECIFICITY; HAMSTER; METABOLISM;

ALCOHOLS; ALKENES; ANIMALS; BINDING, COMPETITIVE; CHO CELLS; COMBINATORIAL CHEMISTRY TECHNIQUES; CRICETINAE; GUANOSINE 5'-O-(3-THIOTRIPHOSPHATE); RECEPTORS, OPIOID, MU; STEREOISOMERISM; SUBSTRATE SPECIFICITY; SULFUR RADIOISOTOPES;

EID: 0038204635     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol027237f     Document Type: Article

References (23)

1. (a) Schreiber, S. L. Science 2000, 287, 1964-1969.
2. (b) Stockwell, B. R. Nat. Rev. Genet. 2000, 1, 116-125.
3. For examples, see: (a) Pelish, H. E.; Westwood, N. J.; Feng, Y.; Kirchhausen, T.; Shair, M. D. J. Am. Chem. Soc. 2001, 123, 6740-6741. (b) Nicolaou, K. C.; Pfefferkorn, J. A.; Mitchell, H. J.; Roecker, A. J.; Barluenga, S.; Cao, G.-Q.; Affleck, R. L.; Lillig, J. E. J. Am. Chem. Soc. 2000, 122, 9954-9967. (c) Tan, D. S.; Foley, M. A.; Shair, M. D.; Schreiber, S. L. J. Am. Chem. Soc. 1998, 120, 8565-8566.
4. For examples, see: (a) Pelish, H. E.; Westwood, N. J.; Feng, Y.; Kirchhausen, T.; Shair, M. D. J. Am. Chem. Soc. 2001, 123, 6740-6741. (b) Nicolaou, K. C.; Pfefferkorn, J. A.; Mitchell, H. J.; Roecker, A. J.; Barluenga, S.; Cao, G.-Q.; Affleck, R. L.; Lillig, J. E. J. Am. Chem. Soc. 2000, 122, 9954-9967. (c) Tan, D. S.; Foley, M. A.; Shair, M. D.; Schreiber, S. L. J. Am. Chem. Soc. 1998, 120, 8565-8566.
5. For examples, see: (a) Pelish, H. E.; Westwood, N. J.; Feng, Y.; Kirchhausen, T.; Shair, M. D. J. Am. Chem. Soc. 2001, 123, 6740-6741. (b) Nicolaou, K. C.; Pfefferkorn, J. A.; Mitchell, H. J.; Roecker, A. J.; Barluenga, S.; Cao, G.-Q.; Affleck, R. L.; Lillig, J. E. J. Am. Chem. Soc. 2000, 122, 9954-9967. (c) Tan, D. S.; Foley, M. A.; Shair, M. D.; Schreiber, S. L. J. Am. Chem. Soc. 1998, 120, 8565-8566.
6. (a) Harrison, B. A.; Verdine, G. L. Org. Lett. 2001, 3, 2157-2159.
7. (b) Gierasch, T. M.; Chytil, M.; Didiuk, M. T.; Park, J. Y.; Urban, J. J.; Nolan, S. P.; Verdine, G. L. Org. Lett. 2000, 2, 3999-4002.
8. (c) Michielin, O.; Zoete, V.; Gierasch, T. M.; Eckstein, J.; Napper, A.; Verdine, G.; Karplus, M. J. Am. Chem. Soc. 2002, 124, 11131-11141.
9. Harrison, B. A.; Gierasch, T. M.; Neilan, C.; Pasternak, G. W.; Verdine, G. L. J. Am. Chem. Soc. 2002, 124, 13352-13353.
10. (a) Zadina, J. E.; Hackler, L.; Ge, L.-J.; Kastin, A. J. Nature 1997, 386, 499-502.
11. (b) Zadina, J. E.; Martin-Schild, S.; Gerall, A. A.; Kastin, A. J.; Hackler, L.; Ge, L.-J.; Zhang, X. Ann. N. Y. Acad. Sci. 1999, 897, 136-144.
12. (a) Pasternak, G. W. Life Sci. 2001, 68, 2213-2219.
13. (b) Standifer, K. M.; Pasternak, G. W. Cell. Signalling 1997, 9, 237-248.
14. (c) Dooley, C. T.; Houghten, R. A. Biopolymers 1999, 51, 379-390.
15. (d) Law, P. Y.; Wong, Y. H.; Loh, H. H. Biopolymers 1999, 51, 440-455.
16. All stereochemical labels are given in the C2 → C8 direction as shown in compounds 2 and 3.
17. Gierasch, T. M.; Shi, Z.; Verdine, G. L. Manuscript submitted.
18. Gordon, E. M.; Godfrey, J. D.; Delaney, N. G.; Asaad, M. M.; Von Langen, D.; Cushman, D. W. J. Med. Chem. 1988, 31, 2199-2211.
19. (a) Blackwell, H. E.; O'Leary, D. J.; Chatterjee, A. K.; Washenfelder, R. A.; Bussmann, D. A.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 58-71.
20. (b) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043.
21. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953-956.
22. (a) Pasternak, G. W. Mod. Methods Pharmacol. 1990, 6, 1-17.
23. (b) Bylund, D. B.; Yamamura, H. I. In Methods in Neurotransmitter Receptor Analysis; Yamamura, H. I., Ed.; Raven: New York, 1990; pp 1-35.