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Volumn 10, Issue 5, 2002, Pages 1207-1219

Coupling of isoprenoid triflates with organoboron nucleophiles: Synthesis and biological evaluation of geranylgeranyl diphosphate analogues

(4) Mu, YongQi a Eubanks, Lisa M b Poulter, C Dale b Gibbs, Richard A a,c

a WAYNE STATE UNIVERSITY (United States)

b UNIVERSITY OF UTAH (United States)

c PURDUE UNIVERSITY (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 CYCLOPROPYL 3 NORGERANYLGERANYLDIPHOSPHATE; 3 PHENYL 1,11,15 TRIMETHYLHEXADECA 14 TETRAENEDIPHOSPHATE; 3 TERT BUTYL 3 NORGERANYLGERANYLDIPHOSPHATE; 3 VINYL 3 NORGERANYLGERANYLDIPHOSPHATE; GERANYLTRANSFERASE; ISOPRENOID; METHYL GROUP; ORGANOBORON DERIVATIVE; PALLADIUM; PYROPHOSPHORIC ACID DERIVATIVE; SILVER; TRANSFERASE INHIBITOR; UNCLASSIFIED DRUG; BORON DERIVATIVE; DITERPENE; ENZYME INHIBITOR; GERANYLGERANYL PYROPHOSPHATE; GERANYLGERANYLTRANSFERASE TYPE I; GERANYLGERANYLTRANSFERASE TYPE-I; ISOPRENOID PHOSPHATE; MESYLIC ACID DERIVATIVE; TERPENE; TRANSFERASE; TRIFLUOROMETHANESULFONIC ACID;

ARTICLE; CATALYSIS; CHEMICAL REACTION; DRUG MECHANISM; ENZYME INACTIVATION; ENZYME INHIBITION; METHYLATION; SUZUKI REACTION; SYNTHESIS; YEAST; CHEMISTRY; DRUG ANTAGONISM; DRUG EFFECT; ENZYME SPECIFICITY; ENZYMOLOGY; KINETICS; METABOLISM; PROTEIN PROCESSING; STRUCTURE ACTIVITY RELATION;

LATEOLABRAX JAPONICUS;

ALKYL AND ARYL TRANSFERASES; BORON COMPOUNDS; DITERPENES; ENZYME INHIBITORS; KINETICS; MESYLATES; POLYISOPRENYL PHOSPHATES; PROTEIN ISOPRENYLATION; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTRATE SPECIFICITY; TERPENES; YEASTS;

EID: 0036191794 PISSN: 09680896 EISSN: None Source Type: Journal
DOI: 10.1016/S0968-0896(01)00390-X Document Type: Article

Times cited : (25)

References (80)

1
- 0029898894
- (1996) Annu. Rev. Biochem. , vol.65 , pp. 241
- Zhang, F.L.¹ Casey, P.J.²

2
- 0033392946
- (1999) Rec. Prog. Horm. Res. , vol.54 , pp. 315
- Fu, H.W.¹ Casey, P.J.²

3
- 0034630098
- (2000) Biochim. Biophys. Acta , vol.1484 , pp. 93
- Sinensky, M.¹

4
- 0034007935
- (2000) Nat. Prod. Rep. , vol.17 , pp. 137
- Harris, C.M.¹ Poulter, C.D.²

5
- 0032564385
- (1998) Biochemistry , vol.37 , pp. 16601
- Strickland, C.L.¹ Windsor, W.T.² Syto, R.³ Wang, L.⁴ Bond, R.⁵ Wu, Z.⁶ Schwartz, J.⁷ Le, H.V.⁸ Beese, L.S.⁹ Weber, P.C.¹⁰

6
- 0034651550
- (2000) Struct. Folding Des. , vol.8 , pp. 209
- Long, S.B.¹ Casey, P.J.² Beese, L.S.³

7
- 0029966304
- (1996) Biol. Chem. , vol.271 , pp. 5289
- Casey, P.J.¹ Seabra, M.C.J.²

8
- 0012698942
- (1989) Proc. Natl. Acad. Sci. U.S.A. , vol.86 , pp. 8323
- Casey, P.J.¹ Solski, P.A.² Der, C.J.³ Buss, J.E.⁴

9
- 0034050541
- (2000) Curr. Opin. Cell. Biol. , vol.12 , pp. 166
- Prendergast, G.C.¹

10
- 0030865773
- (1997) J. Med. Chem. , vol.40 , pp. 2971
- Leonard, D.M.¹

11
- 0030962347
- (1997) Annu. Rev. Pharmacol. Toxicol. , vol.37 , pp. 143
- Gibbs, J.B.¹ Oliff, A.²

12
- 0030749458
- (1997) Biochem. Biophys. Acta , vol.1333
- Cox, A.D.¹ Der, C.J.²

13
- 0033620684
- (1999) Biochem. Biophys. Acta , vol.1423
- Oliff, A.¹

14
- 0032704708
- (1999) J. Clin. Oncol. , vol.17 , pp. 3631
- Rowinsky, E.K.¹ Windle, J.J.² VonHoff, D.D.³

15
- 0030609121
- (1997) Trends Pharm. Sci. , vol.18 , pp. 437
- Omer, C.A.¹ Kohl, N.E.²

16
- 0030749464
- (1997) Pharmacol. Ther. , vol.74 , pp. 103
- Sebti, S.M.¹ Hamilton, A.D.²

17
- 0027413551
- (1993) J. Biol. Chem. , vol.268 , pp. 7617
- Gibbs, J.B.¹ Pompliano, D.L.² Mosser, S.D.³ Rands, E.⁴ Lingham, R.B.⁵ Singh, S.B.⁶ Scolnick, E.M.⁷ Kohl, N.E.⁸ Oliff, A.⁹

18
- 0028941868
- (1995) Biochem. Pharmacol. , vol.49 , pp. 839
- Cohen, L.H.¹ Valentijn, A.R.P.M.² Roodenburg, L.³ Leeuwen, R.E.W.V.⁴ Huismen, R.H.⁵ Lutz, R.J.⁶ Marel, G.A.V.D.⁷ Van Boom, J.H.⁸

19
- 0029025272
- (1995) J. Med. Chem. , vol.38 , pp. 435
- Patel, D.V.¹ Gordon, E.M.² Schmidt, R.J.³ Weller, H.N.⁴ Young, M.G.⁵ Zahler, R.⁶ Barbacid, M.⁷ Carboni, J.M.⁸ Gullo-Brown, J.L.⁹ Hunihan, L.¹⁰ Ricca, C.¹¹ Robinson, S.¹² Seizinger, B.R.¹³ Tuomari, A.V.¹⁴ Manne, V.¹⁵

20
- 0029587277
- (1995) Biochem. Biophys. Res. Commun. , vol.217 , pp. 245
- Kang, M.S.¹ Stemerick, D.M.² Zwolshen, J.H.³ Harry, B.S.⁴ Sunkara, P.S.⁵ Harrison, B.L.⁶

21
- 0030011713
- (1996) Bioorg. Med. Chem. Lett. , vol.6 , pp. 1291
- Lamothe, M.¹ Perrin, D.² Blotieres, D.³ Leborgne, M.⁴ Gras, S.⁵ Bonnet, D.⁶ Hill, B.T.⁷ Halazy, S.⁸

22
- 0031933368
- (1998) Lipids , vol.33 , pp. 39
- Hohl, R.J.¹ Lewis, K.A.² Cermak, D.M.³ Wiemer, D.F.⁴

23
- 0031834743
- (1998) Bioorg. Med. Chem. , vol.6 , pp. 687
- Holstein, S.A.¹ Cermak, D.M.² Wiemer, D.F.³ Lewis, K.⁴ Hohl, R.J.⁵

24
- 0033593920
- (1999) Bioorg. Med. Chem. Lett. , vol.9 , pp. 623
- Barber, A.M.¹ Hardcastle, I.R.² Rowlands, M.G.³ Nutley, B.P.⁴ Marriott, J.H.⁵ Jarman, M.⁶

25
- 0033492218
- (1999) Bioorg. Med. Chem. , vol.7 , pp. 2391
- Schlitzer, M.¹ Sattler, I.²

26
- 0032806605
- (2000) Anticancer Res. , vol.19 , pp. 2117
- Schlitzer, M.¹ Sattler, I.² Dahse, H.M.³

27
- 0028884392
- (1995) J. Org. Chem. , vol.60 , pp. 7821
- Gibbs, R.A.¹ Krishnan, U.² Dolence, J.M.³ Poulter, C.D.⁴

28
- 0029823720
- (1996) J. Org. Chem. , vol.61 , pp. 8010
- Mu, Y.Q.¹ Gibbs, R.A.² Eubanks, L.M.³ Poulter, C.D.⁴

29
- 85047673338
- (1995) Tetrahedron Lett. , vol.36 , pp. 5669
- Mu, Y.Q.¹ Gibbs, R.A.²

30
- 0033598364
- (1999) Med. Chem. , vol.42 , pp. 3800
- Gibbs, B.S.¹ Zahn, T.J.² Mu, Y.Q.³ Sebolt-Leopold, J.⁴ Gibbs, R.A.J.⁵

31
- 0034618188
- (2000) Bioorg. Med. Chem. Lett. , vol.10 , pp. 1763
- Zahn, T.J.¹ Weinbaum, C.² Gibbs, R.A.³

32
- 0029159923
- (1995) Arch. Biochem. Biophys. , vol.321 , pp. 182
- Stirtan, W.G.¹ Poulter, C.D.²

33
- 0027981210
- (1994) Biol. Chem. , vol.269 , pp. 3175
- Zhang, F.L.¹ Diehl, R.E.² Kohl, N.E.³ Gibbs, J.B.⁴ Giros, B.⁵ Casey, P.J.⁶ Omer, C.A.J.⁷

34
- 0028988427
- (1995) Biochemistry , vol.34 , pp. 1344
- Yokoyama, K.¹ McGeady, P.² Gelb, M.H.³

35
- 0030470834
- (1996) Biochem, J. , vol.320 , pp. 925
- Zhang, F.L.¹ Casey, P.J.²

36
- 0030935249
- (1997) Biochemistry , vol.36 , pp. 4552
- Stirtan, W.G.¹ Poulter, C.D.²

37
- 0031055466
- (1997) Biol. Chem. , vol.272 , pp. 3944
- Yokoyama, K.¹ Zimmerman, K.² Scholten, J.³ Gelb, M.H.J.⁴

38
- 0027299926
- (1993) Mol. Cell. Biol. , vol.13 , pp. 4260
- Trueblood, C.E.¹ Ohya, Y.² Rine, J.³

39
- 0027958138
- (1994) Proc. Natl. Acad. Sci. U.S.A. , vol.91 , pp. 1275
- Caldwell, G.A.¹ Wang, S.-H.² Naider, F.³ Becker, J.M.⁴

40
- 0030968859
- (1997) J. Biol. Chem. , vol.272 , pp. 14093
- Rowell, C.A.¹ Kowalczyk, J.J.² Lewis, M.D.³ Garcia, A.M.⁴

41
- 0030923192
- (1997) J. Biol. Chem. , vol.272 , pp. 14459
- Whyte, D.B.¹ Kirschmeier, P.² Hockenberry, T.N.³ Nunez-Oliva, I.⁴ James, L.⁵ Catino, J.J.⁶ Bishop, W.R.⁷ Pai, J.-K.⁸

42
- 0033214457
- (1999) Cancer Res. , vol.59 , pp. 4919
- Sun, J.¹ Blaskovich, M.A.² Knowles, D.³ Qian, Y.⁴ Ohkanada, J.⁵ Bailey, R.D.⁶ Hamilton, A.D.⁷ Sebti, S.M.⁸

43
- 0031814992
- (1998) Am. J. Physiol. , vol.275
- Stark, W.W.¹ Blaskovich, M.A.² Johnson, B.A.³ Qian, Y.⁴ Vasudevan, A.⁵ Pitt, B.⁶ Hamilton, A.D.⁷ Sebti, S.M.⁸ Davies, P.⁹

44
- 0033930168
- (2000) J. Bone Miner. Res. , vol.15 , pp. 1467
- Coxon, F.P.¹ Helfrich, M.H.² Van't Hof, R.³ Sebti, S.⁴ Ralston, S.H.⁵ Hamilton, A.⁶ Rogers, M.J.⁷

45
- 0029938011
- (1996) J. Med. Chem. , vol.39 , pp. 1352
- Macchia, M.¹ Jannitti, N.² Gervasi, G.³ Danesi, R.⁴

46
- 0033594336
- (1999) J. Med. Chem. , vol.42 , pp. 1333
- Vasudevan, A.¹ Qian, Y.² Vogt, A.³ Blaskovich, M.A.⁴ Ohkanada, J.⁵ Sebti, S.M.⁶ Hamilton, A.D.⁷

47
- 0034647876
- (2000) Biochim. Biophys. Acta , vol.1480 , pp. 132
- Smalera, I.¹ Williamson, J.M.² Baginsky, W.³ Leting, B.⁴ Mazur, P.⁵

48
- 0026793014
- (1992) Tetrahedron Lett. , vol.33 , pp. 6299
- Comins, D.L.¹ Dehghani, A.²

49
- 0000764963
- (1992) J. Org. Chem. , vol.57 , pp. 6972
- Crisp, G.T.¹ Meyer, A.G.²

50
- 0028219812
- (1994) Tetrahedron Lett. , vol.35 , pp. 2509
- Gibbs, R.A.¹ Krishnan, U.²

51
- 0008616402
- note

52
- 0033606859
- (1999) Org. Lett. , vol.1 , pp. 627
- Shao, Y.¹ Eummer, J.T.² Gibbs, R.A.³

53
- 33751385493
- (1993) J. Org. Chem. , vol.58 , pp. 2201
- Oh-e, T.¹ Miyaura, N.² Suzuki, A.³

54
- 0027229274
- (1993) Tetrahedron Lett. , vol.34 , pp. 3211
- Yasuda, N.¹ Xavier, L.² Rieger, D.L.³ Li, Y.⁴ DeCamp, A.E.⁵ Dolling, U.-H.⁶

55
- 0025107953
- (1990) Tetrahedron Lett. , vol.31 , pp. 5541
- Soderquist, J.A.¹ Santiago, B.²

56
- 0034609150
- (2000) Tetrahedron Lett. , vol.41 , pp. 6237
- Gray, M.¹ Andrews, I.P.² Hook, D.F.³ Kitteringham, J.⁴ Voyle, M.⁵

57
- 0000131734
- (1991) J. Am. Chem. Soc. , vol.113 , pp. 9585
- Farina, V.¹ Krishnan, B.²

58
- 33751386638
- (1993) J. Org. Chem. , vol.58 , pp. 5434
- Farina, V.¹ Krishnan, B.² Marshall, D.R.³ Roth, G.P.⁴

59
- 0001302995
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 11014
- Johnson, C.R.¹ Braun, M.P.²

60
- 84930641655
- (1994) Synlett , pp. 649
- Gillmann, T.¹ Weeber, T.²

61
- 84913982656
- (1993) Synlett , pp. 573
- Newhouse, B.J.¹ Meyers, A.I.² Sirisoma, N.S.³ Braun, M.P.⁴ Johnson, C.R.⁵

62
- 33845281635
- (1987) Am. Chem. Soc. , vol.109 , pp. 4756
- Uenishi, J.¹ Beau, J.M.² Armstrong, R.W.³ Kishi, Y.J.⁴

63
- 0008613608
- PhD Dissertation, Wayne State University, Detroit, MI, USA
- (1995)
- Braun, M.P.¹

64
- 0025000356
- (1990) Tetrahedron Lett. , vol.31 , pp. 6509
- Roush, W.R.¹ Moriarty, K.J.² Brown, B.B.³

65
- 0026728445
- (1992) Tetrahedron Lett. , vol.33 , pp. 6205
- DeLera, A.R.¹ Torrado, A.² Iglesias, B.³ Lopez, S.⁴

66
- 0000340061
- (1994) Org. Chem. , vol.59 , pp. 5905
- Farina, V.¹ Kapadia, S.² Krishnan, B.³ Wang, C.⁴ Liebeskind, L.S.J.⁵

67
- 0040394615
- (1994) Synlett , pp. 763
- Bouzbouz, S.¹ Kirschleger, B.²

68
- 0026731181
- (1992) Tetrahedron Lett. , vol.33 , pp. 6435
- Corey, E.J.¹ Shieh, W.-C.²

69
- 84987364007
- (1993) Synlett , pp. 783
- Klinge, S.¹ Demuth, M.²

70
- 0031040491
- (1997) Synthesis , pp. 202
- Eis, K.¹ Schmalz, H.-G.²

71
- 0035799332
- (2001) Biochemistry , vol.40 , pp. 3920
- Clausen, E.A.¹ Edelstein, R.L.² Distefano, M.D.³

72
- 33845374468
- (1986) J. Org. Chem. , vol.51 , pp. 4768
- Davisson, V.J.¹ Woodside, A.B.² Neal, T.R.³ Stremler, K.E.⁴ Muehlbacher, M.⁵ Poulter, C.D.⁶

73
- 0000917809
- (1987) Org. Synth. , vol.66 , pp. 211
- Woodside, A.B.¹ Huang, Z.² Poulter, C.D.³

74
- 0001136978
- (1972) Tetrahedron Lett. , pp. 4339
- Corey, E.J.¹ Kim, C.U.² Takeda, M.³

75
- 0027327439
- (1993) Anal. Biochem. , vol.213 , pp. 356
- Zhang, D.¹ Poulter, C.D.²

76
- 0029655869
- (1996) Tetrahedron , pp. 119
- Dolence, J.M.¹ Poulter, C.D.²

77
- 0001437041
- (1992) J. Am. Chem. Soc. , pp. 7945
- Pompliano, D.L.¹ Gomez, R.P.² Anthony, N.J.³

78
- 0003692166
- (2000) Biochemistry , pp. 2593
- Huang, C.-C.¹ Hightower, K.E.² Fierke, C.A.³

79
- 0035907478
- (2001) Bioorg. Med. Chem. Lett. , vol.11 , pp. 1605
- Zahn, T.J.¹ Whitney, J.² Weinbaum, C.³ Gibbs, R.A.⁴

80
- 0000779263
- (1978) J. Org. Chem. , vol.43 , pp. 4915
- Coates, R.M.¹ Ley, D.A.² Cavender, P.L.³

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