Synthesis of novel α-C-glycosylamino acids and reverse regioselectivity in larock’s heteroannulation for the synthesis of the indole nucleus

Bioscience, Biotechnology and Biochemistry

Volumn 66, Issue 10, 2002, Pages 2273-2278

  Nishikawa, Toshio ^a   Wada, Kyoko ^a   Isobe, Minoru ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

C glycosylamino acid; Indole; Iso tryptophan; Palladium catalyst; Propargyl glycine

Indexed keywords

3 IODOANILINE; 3-IODOANILINE; AMINO ACID; ANILINE DERIVATIVE; COPPER; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; GLYCOSIDE; INDOLE DERIVATIVE; PALLADIUM; SERINE; ZINC;

ARTICLE; CATALYSIS; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OPTICAL ROTATION; SYNTHESIS;

AMINO ACIDS; ANILINE COMPOUNDS; CATALYSIS; COPPER; GLYCOSIDES; INDICATORS AND REAGENTS; INDOLES; MAGNETIC RESONANCE SPECTROSCOPY; OPTICAL ROTATION; PALLADIUM; SERINE; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROPHOTOMETRY, INFRARED; ZINC;

EID: 0142099039     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.66.2273     Document Type: Article

References (39)

1. Dondoni, A., and Marra, A., Methods for anomeric carbon-linked and fused sugar amino acid synthesis: The gateway to artificial glycopeptides. Chem. Rev., 100, 4395-4421 (2000).
2. Nishikawa, T., Ishikawa, M., and Isobe, M., Synthesis of a a-C-mannosyltryptophan derivative, naturally occurring C-glycosyl amino Acid found in human ribonuclease. Synlett, 123-125 (1999).
3. Nishikawa, T., Ishikawa, M., Wada, K., and Isobe, M., Total synthesis of a-C-mannosyltryptophan, a naturally occurring C-glycosylamino acid. Synlett, 945-947 (2001).
4. 2-a-L-C-mannosylpyranosyl- L-tryptophan. J. Am. Chem. Soc., 121, 123-125 (1999).
5. Vliegenthart, J. F. G., and Casset, F., Novel forms of protein glycosylation. Current Opinion in Structural Biology, 8, 565-571 (1998).
6. Furmanek, A., and Hofsteenge, J., Protein C-man-nosylation: Facts and questions. Acta Biochimica Polonica, 47, 781-789 (2000).
7. Larock, R. C., and Yum, E. K., Synthesis of indoles via palladium-catalyzed heteroannulation of internal alkynes. J. Am. Chem. Soc., 113, 6689-6690 (1991).
8. Larock, R. C., Yum, E. K., and Refvik, M. D., Synthesis of 2,3-disubstituted indoles via palladium-catalyzed annulation of internal alkynes. J. Org. Chem., 63, 7652-7662 (1998).
9. Isobe, M., Nishizawa, R., Hosokawa, S., and Nishikawa, T., Stereocontrolled synthesis and reactivity of sugar acetylene. Chem. Commun., 2665-2676 (1998).
10. Isobe, M., and Kira, K., New synthesis with acetylene biscobalthexacarbonyl complex. J. Synth. Org. Chem. Jpn. (in Japanese), 58, 23-30, 99-107 (2000).
11. Dondoni, A., Mariotti, G., and Marra, A., General, stereoselective synthesis of ethylene isosterers of a-and b-glycosylasparagines. Tetrahedron Lett., 41, 3483-3486 (2000).
12. Turner, J. J., Leeuwenburgh, M. A., van der Marel, G. A., and van Boom, J. H., A convenient route to a-amino acids with b-alkyne substituents from a serine derived aziridine. Tetrahedron Lett., 42, 8713-8716 (2001).
13. Church, N. J., and Young, D. W., Synthesis of stereospecifically labeled D-prop-2-ynylglycine and investigation of the action of D-amino acid oxidase. J. Chem. Soc. Chem. Commun., 943-944 (1994).
14. Bajgrowicz, J. A., Hallaoui, A. El., Jacquier, R., Pigiere, Ch., and Viallefont, Ph., Lithium dior-ganocuprate reactions with L-serine derivatives. Tetrahedron Lett., 25, 2759-2762 (1984).
15. Dureault, A., Tranchenpain, I., and Depezay, J.-C., Nucleophilic opening of chiral bis(aziridines): A route to enantiomerically pure a-amino aldehyde or acids and polysubstitiuted piperidines. J. Org. Chem., 54, 5324-5330 (1989).
16. Church, N. J., and Young, D. W., Synthesis of the suicide substrate D-propargylglycine stereospecifically labeled with deuterium and investigation of its oxidation by D-amino acid oxidase. J. Chem. Soc. Perkin Trans 1, 8, 1475-1482 (1998).
17. Knochel, P., Chou, T.-S., Chen, H. G., Yeh, M. C. P., and Rozema, M. J., Nucleophilic reactivity of zinc and copper carbenoids, 2. J. Org. Chem., 54, 5202-5204 (1989).
18. Yeh, M. C., and Knochel, P., The reactivity of the highly functionalized copper, zinc reagents RCu(CN)ZnI toward 1-haloalkynes and acetylenic esters. Tetrahedron Lett., 30, 4799-4802 (1989).
19. Dunn, N. J., Jackson, R. F. W., Pietruszka, J., Wishart, N., Ellis, D., and Wythes, M. J., Preparation of serine-derived organozinc reagents in tetra-hydrofuran: Synthesis of novel enantiomerically pure allenic, acetylenic and heteroaryl amino acids. Syn-lett, 499-500 (1993).
20. Dunn, N. J., Jackson, R. F. W., Pietruszka, J., and Turner, D., Synthesis of enantiomerically pure unsaturated a-amino acids using serine-derived zinc/copper reagents. J. Org. Chem., 60, 2210-2215 (1995).
21. Southwick, P. L., and Kirchner, J. R., The mor-pholine-iodophenylacetylene adduct or charge-tran-sfer complex. Formation and conversion to N-styrylmorpholine. J. Org. Chem., 27, 3305-3308 (1962).
22. Goekjian, P. G., Wu, T.-C., Kang, H.-Y., and Kishi, Y., Preferred conformation of C-glycosides. 7. Preferred conformation of carbon analogues of isomaltose and gentiobiose. J. Org. Chem., 56, 6422-6434 (1991).
23. Tamaru, Y., Tanigawa, H., Yamamoto, T., and Yoshida, Z., Copper(I)-promoted Michael-addition reaction of organozincs of esters, nitriles, and a-ami-no acids. Angew. Chem. Int. Ed., 28, 351-353 (1989).
24. Knochel, P., and Singer, R. D., Preparation and reactions of polyfunctional organozinc reagents in organic synthesis. Chem. Rev., 93, 2117-2188 (1993).
25. Although optimization has not been performed, the formation of by-product 10 was suppressed by reducing the amount of zinc dust used. The galactose analog of 12 was synthesized in a similar manner.
26. Kornfeld, E. C., The synthesis of “isotryptophan”, a-amino-b-(2-indole)-propionic acid. J. Org. Chem., 16, 806-809 (1951).
27. Ma, C., Yu, S., He, X., Liu, X., and Cook, J. M., Efficient asymmetric synthesis of important tryptophan analogs for biological research via the Schollkopf chiral auxiliary. Tetrahedron Lett., 41, 2781-2785 (2000).
28. The NMR spectra of 13c and 13d were measured at 80°C to sharpen the signals, because the spectra measured at rt gave heavily broadening signals, especially of the protons of the pyranose ring. This fact indicated the conformational flexibility of these products.
29. Larock, C. R., Review, palladium-catalyzed annula-tion. J. Organomet. Chem., 576, 111-124 (1999).
30. Chen, C., Lieberman, D. R., Street, L. J., Guiblin, A. R., Larsen, R. D., and Verhoeven, T. R., An efficient synthesis of the indole acetic acid metabolite of MK-0462. Synth. Commun., 26, 1977-1984 (1996).
31. Zhang, H.-C., Brumfield, K. K., and Maryanoff, B. E., Synthesis of trisubstituted indoles on the solid phase via palladium-mediated heteroannulation of internal alkynes. Tetrahedron Lett., 38, 2439-2442 (1997).
32. Ujjainwalla, F., and Warner, D., Synthesis of 5-, 6-and 7-azaindoles via palladium-catalyzed heteroannu-lation of internal alkynes. Tetrahedron Lett., 39, 5355-5358 (1998).
33. Park, S. S., Choi, J.-K., and Yum, E. K., A facile synthesis of 2,3-disubstituted pyrrolo[2,3-b]pyridines via palladium-catalyzed heteroannulation with internal alkynes. Tetrahedron Lett., 39, 627-630 (1998).
34. Zhang, H.-C., Ye, H., White, K. B., and Maryanoff, B. E., Efficient synthesis of 3-substituted 2-arylin-doles via Suzuki coupling reactions on the solid phase. Tetrahedron Lett., 42, 4751-4754 (2001).
35. Jeschke, T., Wensbo, D., Annby, U., Gronowitz, S., and Cohen, L. A., A novel approach to Bz-substitut-ed tryptophans via Pd-catalyzed coupling/annula-tion. Tetrahedron Lett., 34, 6471-6474 (1993).
36. Ma, C., Liu, X., Yu, S., Zhao, S., and Cook, J. M., Concise synthesis of optically active ring-A substituted tryptophans. Tetrahedron Lett., 40, 657-660 (1999).
37. Ma, C., Liu, X., Li, X., Flippen-Anderson, J., Yu, S., and Cook, J. M., Efficient asymmetric synthesis of biologically important tryptophan analogues via a palladium-mediated heteroannulation reaction. J. Org. Chem., 66, 4525-4542 (2001).
38. Rutjies, F. P. J. T., Wolf, L. B., and Schoemaker, H. E., Applications of aliphatic unsaturated non-proteinogenic a-H-a-amino acids. J. Chem. Soc., Perkin Trans. 1, 4197-4212 (2000).
39. Walsh, C., Suicide substrate: mechanism based enzyme inactivators. Tetrahedron, 38, 871-909 (1982).