RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2009(19): 3179-3210
DOI: 10.1055/s-0029-1216976
DOI: 10.1055/s-0029-1216976
REVIEW
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of Glycosyltransferase Inhibitors
Weitere Informationen
Received
12 May 2009
Publikationsdatum:
03. September 2009 (online)
Publikationsverlauf
Publikationsdatum:
03. September 2009 (online)
Abstract
Glycosyltransferases and glycosidases work together to construct the oligosaccharide moieties of biologically active glycoconjugates. Although many excellent glycosidase inhibitors have been developed, some of which are in clinical use, there are relatively few promising candidates of glycosyltransferase inhibitors. In this review, we summarize the current state of the development of glycosyltransferase inhibitors.
1 Introduction
2 Basic Strategy for Designing Glycosyltransferase Inhibitors
3 Sugar Nucleotide Analogues
4 Analogues of Acceptor Oligosaccharides (Acceptor
Analogues)
5 Bisubstrate Inhibitors
6 High-Throughput Screening: Discovering Structurally
Simple
Inhibitors
7 Antisense Inhibitors
8 Questions and Future Directions
Key words
glycosyltransferases - inhibitors - transition-state analogues - sugar nucleotides - oligosaccharides
- 1 For example:
Introduction
to Glycobiology
Taylor ME.Drickamer K. Oxford University Press; Oxford: 2003. - 2
Handbook
of Glycosyltransferases and Related Genes
Taniguchi N.Honke K.Fukuda M. Springer Verlag; Berlin: 2001. - 3
Kajimoto T.Node M. Curr. Top. Med. Chem. 2009, 9: 13 -
4a
Gastinel LN.Cambillau C.Bourne Y. EMBO J. 1999, 18: 3546 -
4b
Chanock SJ.Davies GJ. Biochemistry 1999, 38: 6380 -
4c
Ünligil UM.Zhou S.Yuwaraj S.Sarkar M.Schachter H.Rini JM. EMBO J. 2000, 19: 5269 -
4d
Pederson LC.Tsuchida K.Kitagawa H.Sugahara K.Darden TA.Negishi M. J. Biol. Chem. 2000, 275: 34580 -
4e
Persson K.Ly HD.Dieckelmann M.Wakarchuk WW.Withers SG.Strynadka NCJ. Nature Struct. Biol. 2001, 8: 166 -
4f
Gastinel LN.Bignon C.Misra AK.Hindsgaul O.Shaper JH.Joziasse DH. EMBO J. 2001, 20: 638 -
4g
Boix E.Zhang Y.Swaminathan GJ.Brew K.Acharya KR. J. Biol. Chem. 2002, 277: 28310 -
4h
Qsba PK.Ramakrishnan B.Boeggeman E. Curr. Drug Targets 2008, 9: 292 - According to the assay for glycosyltransferases; see, for example:
-
5a
Palcic M.Sujino K. Trends Glycosci. Glycotechnol. 2001, 13: 361 -
5b
Wongkongkatep J.Miyahara Y.Ojida A.Hamachi I. Angew. Chem. Int. Ed. 2006, 45: 665 ; and references therein - See also:
-
6a
Compain P.Martin OR. Bioorg. Med. Chem. 2001, 9: 3077 -
6b
Jung K.-H.Schwörer R.Schmidt RR. Trends Glycosci. Glycotechnol. 2003, 15: 275 -
6c
Wang X.Zhang L.-H.Ye X.-S. Med. Res. Rev. 2003, 23: 32 -
6d
Zou W. Curr. Top. Med. Chem. 2005, 5: 1363 - 7
Ichikawa Y.Lin Y.-C.Dumas DP.Shen G.-J.Garcia-Junceda E.Williams MA.Bayer R.Ketcham C.Walker LE.Paulson JC.Wong C.-H. J. Am. Chem. Soc. 1992, 114: 9283 - For example:
-
8a
Withers SG.Street IP. J. Am. Chem. Soc. 1988, 110: 8551 -
8b
McCarter JD.Withers SG. J. Am. Chem. Soc. 1996, 118: 241 -
8c
William SJ.Withers SG. Carbohydr. Res. 2000, 327: 27 -
9a
Thoden JB.Hegeman AD.Wesenberg G.Chapeau MC.Frey PA.Holden HM. Biochemistry 1997, 36: 6294 -
9b
Murray BW.Wittmann V.Burkart MD.Hung S.-C.Wong C.-H. Biochemistry 1997, 36: 823 -
10a
Korytnyk W.Valentekovic-Horvat S. Tetrahedron Lett. 1980, 21: 1493 -
10b
Tius MA. Tetrahedron 1995, 51: 6605 - 11
Hayashi T.Murray BW.Wang R.Wong C.-H. Bioorg. Med. Chem. 1997, 5: 497 - 12
Thomas P.Bassel EM.Westwood JH. Biochem. J. 1974, 139: 661 -
13a
Wong C.-H.Haynie SL.Whitesides GM. J. Org. Chem. 1982, 47: 5418 -
13b
Wong C.-H.Wang R.Ichikawa Y. J. Org. Chem. 1992, 57: 4343 - 14
Heidlas JE.Lees WJ.Whitesides GM. J. Org. Chem. 1992, 57: 152 -
15a
Morrison JF.Ebner KE. J. Biol. Chem. 1971, 246: 3977 -
15b
Babad H.Hassid WZ. J. Biol. Chem. 1966, 241: 2672 -
16a
Hindsgaul O.Kaur KJ.Srivastava G.Thurin M.Crawley SC.Heerze LD.Palcic MM. J. Biol. Chem. 1991, 266: 17858 -
16b
Sujino K.Malet C.Hindsgaul O.Palcic MM. Carbohydr. Res. 1998, 305: 483 -
16c
Blanken WM.van Eijnden DH. J. Biol. Chem. 1985, 260: 12927 - 17
Takayama S.Chung SJ.Igarashi Y.Ichikawa Y.Sepp A.Lechler RI.Wu J.Hayashi T.Siuzdak G.Wong C.-H. Bioorg. Med. Chem. 1999, 7: 401 -
18a
Stavber S.Zupan M. Tetrahedron Lett. 1994, 35: 1105 -
18b
Burkart MD.Zhang Z.Hung S.-C.Wong C.-H. J. Am. Chem. Soc. 1997, 119: 11743 -
18c
Vincent SP.Burkarrt MD.Tsai C.-Y.Zhang Z.Wong C.-H. J. Org. Chem. 1999, 64: 5264 - 19
Burkart MD.Vincent SP.Duffels A.Murray BM.Ley SV.Wong C.-H. Bioorg. Med. Chem. 2000, 8: 1937 - 20
Wittmann V.Wong C.-H. J. Org. Chem. 1997, 62: 2144 - 21
Baish G.Öhrlein R.Katopodis A.Streiff M.Kolbinger F. Bioorg. Med. Chem. Lett. 1997, 7: 2447 - 22
Burkart MD.Vincent SP.Wong C.-H. Chem. Commun. 1999, 1525 - 23
Chappell MD.Halcomb RL. J. Am. Chem. Soc. 1997, 119: 3393 - 24
Weinstein J.deSousa-e-Silva U.Paulson JC. J. Biol. Chem. 1982, 257: 13825 - 25
Dohi H.Périson S.Durka M.Bosco M.Roué Y.Moreau F.Grizot S.Ducruit A.Escaich S.Vincent SP. Chem. Eur. J. 2008, 14: 9530 - 26
Grizot S.Salem M.Vongsouthi V.Durand L.Moreau F.Dohi H.Vincent SP.Escaich S.Ducruix A. J. Mol. Biol. 2006, 363: 383 - 27
Hartman MCT.Coward JK. J. Am. Chem. Soc. 2002, 124: 10036 - 28
Busca P.Martin OR. Tetrahedron Lett. 1998, 39: 8101 - 29
Lee J.Coward JK. J. Org. Chem. 1992, 57: 4126 - 30
Hartman MCT.Jiang S.Rush JS.Waechter CJ.Coward JK. Biochemistry 2007, 46: 11630 - 31
Tanaka T.Ozawa M.Miura T.Inazu T.Tsuji S.Kajimoto T. Synlett 2002, 1487 - 32
Nakahara S.Tanaka T.Noguchi K.Nozaki K.Tsuji S.Miura T.Kajimoto T. Heterocycles 2004, 63: 779 - 33
Kijima-Suda I.Miyamoto Y.Toyoshima S.Itoh M.Osawa T. Cancer Res. 1986, 46: 858 - 34
Seo K.-C.Kwon Y.-G.Kim D.-H.Jang I.-S.Cho J.-W.Chung S.-K. Chem. Commun. 2009, 1733 - 35
Yu SH.Chung SK. Tetrahedron: Asymmetry 2005, 16: 2729 -
36a
Kolb H.-C.Sharpless KB. Tetrahedron 1992, 48: 10515 -
36b
Balani SK.Brannigan IN.Boyd DR.Sharma ND.Hempenstall F.Smith A. J. Chem. Soc., Perkin Trans. 1 2001, 1090 - 37
Yuasa H.Palcic MM.Hindsgaul O. Can. J. Chem. 1995, 73: 2190 -
38a
Cai S.Stround MR.Hakomori S.Toyokuni T. J. Org. Chem. 1992, 57: 6693 -
38b
Norris AJ.Whitelegge JP.Strouse MJ.Faull KF.Toyokuni T. Bioorg. Med. Chem. Lett. 2004, 14: 571 -
41a
Müller B.Schaub C.Schmidt RR. Angew. Chem. Int. Ed. 1998, 37: 2893 ; in this paper, Schmidt referred the inhibitors designed with focusing on the feature of structural change of sugar nucleotides in the transition state as ‘transition-state analogue inhibitors’ -
41b
Schröder PN.Giannis A. Angew. Chem. Int. Ed. 1999, 38: 1379 -
41c
Skropeta D.Schwörer R.Schmidt RR. Bioorg. Med. Chem. Lett. 2003, 13: 3351 - 40
Kajiwara Y.Ebata T.Koseki K.Kodama H.Matsushita H.Hashimoto H. J. Org. Chem. 1995, 60: 5732 - 41
Amann F.Schaub C.Müller B.Schmidt RR. Chem. Eur. J. 1998, 4: 1106 - 42
Berkowith DB.Sloss DG. J. Org. Chem. 1995, 60: 7047 - 43
Schwörer R.Schmidt RR. J. Am. Chem. Soc. 2002, 124: 1632 - 44
Roy R.Tropper RD. Can. J. Chem. 1991, 69: 817 - 45
Horton D. Methods Carbohydr. Chem. 1972, 6: 282 - 46
Paulsen H.Helpap B. Crabohydr. Res. 1991, 262: 195 - 47
Schmidt RR.Frische K. Bioorg. Med. Chem. Lett. 1990, 3: 1747 - 48
Sun H.Yang J.Amaral KE.Horenstein BA. Tetrahedron Lett. 2001, 42: 2451 - 49
Elain J.Young P.Horenstein NA. Tetrahedron Lett. 2004, 45: 9505 - 50
Kobertz WR.Bertozzi CR.Bednarski MD. Tetrahedron Lett. 1992, 33: 737 - 51
Schäfer A.Thiem J. J. Org. Chem. 2000, 65: 24 - 52
Waldscheck B.Streiff M.Notz W.Kinzy W.Schmidt RR. Angew. Chem. Int. Ed. 2001, 40: 4007 - 53
Luengo JI.Gleason JG. Tetrahedron Lett. 1992, 33: 6911 - 54
Chatani N.Ikeda T.Sano T.Sonoda N.Kurosawa H.Kawasaki Y.Murai S. J. Org. Chem. 1988, 53: 3387 - 55
Cupps TL.Wise DS.Townsend LB. J. Org. Chem. 1982, 47: 5115 - 56
Kozkowski AP.Sorgi KL. Tetrahedron Lett. 1982, 23: 2281 - 57
Mitchell ML.Tian F.Lee LV.Wong C.-H. Angew. Chem. Int. Ed. 2002, 41: 3041 - 58
Mori M.Ito Y.Ogawa T. Carbohydr. Res. 1989, 192: 131 - 59
Schuster M.Blechert S. Bioorg. Med. Chem. Lett. 2001, 11: 1809 -
60a
Wang Y.-F.Dumas D.Wong C.-H. Tetrahedron Lett. 1993, 34: 403 -
60b
Schuster M.Blechert S. Tetrahedron: Asymmetry 1999, 10: 3139 - 61
Flessner T.Wong C.-H. Tetrahedron Lett. 2000, 41: 7805 -
62a
Martin TJ.Brescello R.Toepfer A.Schmidt RR. Glycoconj. J. 1993, 10: 16 -
62b
Martin TJ.Schmidt RR. Tetrahedron Lett. 1992, 33: 6123 - 63
Imamura M.Hashimoto H. Tetrahedron Lett. 1996, 37: 1451 -
64a
Kondo H.Ichikawa Y.Wong C.-H. J. Am. Chem. Soc. 1992, 114: 8748 -
64b
Sim MM.Kondo H.Wong C.-H. J. Am. Chem. Soc. 1993, 115: 2260 - 65
Müller B.Martin TJ.Schaub C.Schmidt RR. Tetrahedron Lett. 1998, 39: 509 - 66
Daub GW.van Tameken EE. J. Am. Chem. Soc. 1977, 99: 3526 - 67
Izumi M.Wada K.Yuasa H.Hashimoto H. J. Org. Chem. 2005, 70: 8817 - 68
Paulsen H.Matschulat P. Liebigs Ann. Chem. 1991, 487 - 69
Vaghefi MM.Bernacki RJ.Dalley NK.Wilson BE.Robins RK. J. Med. Chem. 1987, 30: 1383 - 70
Furusawa K.Sekine M.Hata T. J. Chem. Soc., Perkin Trans. 1 1976, 1711 - 71
Vaghefi MM.Bernacki RJ.Hennen WJ.Robins RK. J. Med. Chem. 1987, 30: 1391 - 72
Jones SS.Rayner R.Reese CB.Ubasawa A.Ubasawa M. Tetrahedron 1980, 36: 3075 - 73
Hajduch J.Nam G.Kim EJ.Fröhlich R.Hanover JA.Kirk KL. Carbohydr. Res. 2008, 343: 189 - 74
Chang R.Vo T.-T.Finney NS. Carbohydr. Res. 2006, 341: 1998 - 75
Cui J.Horton D. Carbohydr. Res. 1998, 309: 319 - 76
McGavey GJ.Benendum TE.Schmidtmann FW. Org. Lett. 2002, 4: 3591 - 77
Khaled A.Piotrowska O.Dominiak K.Augé C. Carbohydr. Res. 2008, 343: 167 - 78
Lairson LL.Wakarchuk WW.Withers SGJ. Chem. Commun. 2007, 365 - 79
Crachon G.Chrétien F.Delannoy P.Verbert A.Chapleur Y. Tetrahedron Lett. 2001, 42: 8821 - 80
Camarasa M.-J.Fernadez-Resa P.Garcia-Lopez M.-T.De Las Heras FG.Mendez-Castrillon PP.Alarcon B.Carrasco L. J. Med. Chem. 1985, 28: 40 - 81
Takatsuki A.Arima K.Tamura G. J. Antibiot. 1971, 215 - 82
Wang R.Steensma DH.Takaoka Y.Yun JW.Kajimoto T.Wong C.-H. Bioorg. Med. Chem. 1997, 5: 661 - 83
Ballell L.Young RJ.Field RA. Org. Biomol. Chem. 2005, 3: 1109 -
84a
König WA.Hahn H.Rathman R.Hass W.Keckeisen A.Hagenmaiser H.Bormann C.Dehler W.Kurth R.Zahner H. Liebigs Ann. Chem. 1986, 407 -
84b
Saksena AK.Lovery RG.Girijivallabhan VM.Guzik H.Ganguly A. Tetrahedron Lett. 1993, 34: 3267 -
85a
Suzuki S.Isono K.Nagatsu J.Mizutani T.Kawashima Y.Mizuno T. J. Antibiot., Ser. A 1965, 18: 131 -
85b
Isono K.Asahi K.Suzuki S. J. Am. Chem. Soc. 1969, 91: 7490 - 86
Tanaka T.Tsuda C.Miura T.Inazu T.Tsuji S.Nishihara S.Hisamatsu M.Kajimoto T. Synlett 2004, 243 - 87
Schaub C.Müller B.Schmidt RR. Glycoconj. J. 1998, 15: 345 -
88a
Shing TMK.Tang Y. Tetrahedron 1991, 47: 4571 -
88b
Lesuisse D.Berchtold GA. J. Org. Chem. 1985, 50: 888 -
88c
Phillipe M.Sepulchre AM.Gero SD.Loibner H.Streicher W.Stutz P. J. Antibiot. 1982, 35: 1507 - 89
Freeze SJ.Vann WF. Carbohydr. Res. 1996, 281: 313 - 90
Kolb HC.Finn MG.Sharpless KB. Angew. Chem. Int. Ed. 2001, 40: 2004 - 91
Lewis WG.Green LG.Grynszpan F.Radic Z.Carlier PR.Taylor P.Finn MG.Sharpless KB. Angew. Chem. Int. Ed. 2002, 41: 1053 - 92
Rostovtsev VV.Green LG.Fokin VV.Sharpless KB. Angew. Chem. Int. Ed. 2002, 41: 2596 - 93
Tornøe CW.Christensen C.Meldal M. J. Org. Chem. 2002, 67: 3057 - 94
Murray BW.Takayama S.Schultz J.Wong C.-H. Biochemistry 1996, 35: 11183 - 95
de Vries T.Palcic M. P.Schoenmakers PS.van den Eijnden D. H.Joziasse D. H. Glycobiology 1997, 7: 921 - 96
Miura Y.Kim S.Etchison JR.Ding Y.Hindsgaul O.Freeze H. Glycoconjugate J. 1999, 16: 725 - 97
Fazio F.Bryan MC.Blixt O.Paulson JC.Wong C.-H. J. Am. Chem. Soc. 2002, 124: 14397 - 98
Lee LV.Mitchell ML.Huang S.-J.Fokin VV.Sharpless KB.Wong C.-H. J. Am. Chem. Soc. 2003, 125: 9588 - 99
Sun H.-Y.Lin S.-W.Ko T.-P.Pan J.-F.Liu C.-L.Lin C.-N.Wang AH.-J.Lin C.-H. J. Biol. Chem. 2007, 282: 9973 - 100
Takaya K.Nakahori N.Kurogochi M.Furuike T.Miura N.Monde K.Lee YC.Nishimura S. J. Med. Chem. 2005, 48: 6054 - 101
Khan SH.Crawley SC.Kanie O.Hindsgaul O. J. Biol. Chem. 1993, 268: 2468 - 102
Kajiwara Y.Kodama H.Watabayashi T.Sato K.Hashimoto H. Carbohydr. Res. 1993, 247: 179 - 103
Lowary TL.Hindsgaul O. Carbohydr. Res. 1993, 249: 163 - 104
Xia J.Xue J.Locke RD.Chandrasekaran EV.Srikrishman T.Matta KL. J. Org. Chem. 2006, 71: 3696 - 105
Card PJ.Reddy CS. J. Org. Chem. 1983, 48: 4734 - 106
Meyer W.Reckendorf MZ. Methods Carbohydr. Res. 1972, 6: 129 - 107
Palcic MMD.Heerze LP.Srivastava O.Hindsgaul O. J. Biol. Chem. 1989, 264: 17174 - 108
Endo T.Kajiwara Y.Kodama H.Hashimoto H. Bioorg. Med. Chem. 1996, 4: 1939 - 109
Hashimoto H.Endo T.Kajiwara Y. J. Org. Chem. 1997, 62: 1914 -
110a
Dennis JW.Laferte S.Waghorne C.Breitman ML.Kerbel RS. Science 1987, 236: 582 -
110b
Ihara S.Miyoshi E.Ko J.Murata K.Nakahara S.Honke K.Dickson RB.Lin C.-Y.Taniguchi N. J. Biol. Chem. 2002, 277: 16960 - 111
Inamori K.Endo T.Ide Y.Fujii S.Gu J.Honke K.Taniguchi N. J. Biol. Chem. 2003, 278: 43102 -
112a
Ando H.Manabe S.Nakahara Y.Ito Y. J. Am. Chem. Soc. 2001, 123: 3848 -
112b
Ando H.Manabe S.Nakahara Y.Ito Y. Angew. Chem. Int. Ed. 2001, 40: 4725 -
112c
Ito Y.Manabe S. Chem. Eur. J. 2002, 8: 3076 -
112d
Hanashima S.Manabe S.Ito Y. Synlett 2003, 979 - 113
Jian L.Hartley C.Chen TH. Chem. Commun. 1996, 2193 - 114
Hanashima S.Manabe S.Inamori K.Taniguchi N.Ito Y. Angew. Chem. Int. Ed. 2004, 43: 5674 -
115a
Hodosi G.Kováč P. J. Am. Chem. Soc. 1997, 119: 2335 -
115b
Hodosi G.Kováč P. Carbohydr. Res. 1998, 308: 63 - 116
Hanashima S.Inamori K.Manabe S.Taniguchi N.Ito Y. Chem. Eur. J. 2006, 12: 3449 -
117a
Hinou H.Sun X.-L.Ito Y. J. Org. Chem. 2003, 68: 5602 -
117b
Hinou H.Sun X.-L.Ito Y. Tetrahedron Lett. 2002, 43: 9147 -
118a
Konradsson P.Mootoo DR.McDevitt RE.Fraiser-Reid B. J. Chem. Soc., Chem. Commun. 1990, 270 -
118b
Veeneman GH.van Leewen SH.van Boom JH. Tetrahedron Lett. 1990, 31: 1331 - 119
Heskamp BM.Veeneman GH.van der Marel GA.van Boeckel CAA.van Boom JH. Tetrahedron 1995, 51: 8397 -
120a
Wong C.-H.Dumas DP.Ichikawa Y.Koseki K.Danishefsky DJ.Weston BW.Lown JB. J. Am. Chem. Soc. 1992, 114: 7321 -
120b
Ichikawa Y.Lin Y.-C.Dumas DP.Shen G.-J.Garcia-Jucenda E.Williams MA.Bayer R.Ketcham C.Walker LE.Paulson JC.Wong C.-H. J. Am. Chem. Soc. 1992, 114: 9283 -
121a
Qiao L.Murray BW.Shimazaki M.Schultz J.Wong C.-H. J. Am. Chem. Soc. 1996, 118: 7653 -
121b
Gamberucci A.Innocenti B.Fulceri R.Banhegyi G.Guinna R.Poxxan T.Benedetti A. J. Biol. Chem. 1994, 269: 23597 - 122
Izumi M.Kaneko S.Yuasa H.Hashimoto H. Org. Biomol. Chem. 2006, 4: 681 - 123
Cao SD.Hernadez-Mateo F.Roy R. J. Carbohydr. Chem. 1998, 17: 609 - 124
Binch H.Stangier K.Thiem J. Carbohydr. Res. 1998, 306: 409 - 125
Pojer PM.Angyal SJ. Aust. J. Chem. 1978, 31: 1031 - 126
Ziegler T.Dettmann R. .Zettl U. J. Carbohydr. Chem. 1999, 18: 1079 - 127
Schmidt RR.Wegmann B.Jung KH. Liebigs Ann. Chem. 1991, 121 - 128
Tsuruta O.Yuasa H.Hashimoto H.Sujino K.Otter A.Li H.Palcic MM. J. Org. Chem. 2003, 68: 6400 - 129
Gross B. J.Swoboda J. G.Walker S. J. Am. Chem. Soc. 2008, 130: 440 - 130
Hart G.Housley MP.Slawson C. Nature 2007, 446: 1017 - 131
Gerken TA.Raman J.Fritz TA.Jamison O. J. Biol. Chem. 2006, 281: 32403 - 132
Kreppel L.Hart GW. J. Biol. Chem. 1999, 274: 32015 - 133
Kemmner W.Hohaus K.Schlag PM. FEBS Lett. 1997, 409: 347 - 134
Zeng G.Li DD.Gao L.Birklé S.Bieberich E.Tokuda A.Yu RK. Biochemistry 1999, 38: 8762 - 135
Lucas R.Balbuena P.Errey JC.Squire MA.Gurcha SS.McNeil M.Besra GS.Davis BG. ChemBioChem 2008, 9: 2197 - 136
Sihelniková L.Kozmon S.Tvaroška I. Collect. Czech. Chem. Commun. 2008, 73: 591