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Journal of Organic Chemistry

Volumn 66, Issue 19, 2001, Pages 6381-6388

Synthesis of L-4,4-difluoroglutamic acid via nucleophilic addition to a chiral aldehyde

(6) Ding, Y a Wang, J a,b Abboud, K A a Xu, Y a,c Dolbier Jr , W R a Richards, N G J a

a University of Florida ^* (United States)

b Triad Therapeutics Inc (United States)

c CLARIANT CORPORATION (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACID HYDROLYSIS;

ADDITION REACTIONS; ENZYMES; FLUORINE; HYDROLYSIS; SYNTHESIS (CHEMICAL);

ORGANIC ACIDS;

4,4 DIFLUOROGLUTAMIC ACID; AMINOALDEHYDE; GLUTAMIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; ENANTIOMER; HYDROLYSIS; REACTION ANALYSIS; SYNTHESIS;

ALDEHYDES; ASPARTATE-AMMONIA LIGASE; GLUTAMATES; HYDROLYSIS; HYDROXYLATION; MOLECULAR CONFORMATION;

EID: 0035929380 PISSN: 00223263 EISSN: None Source Type: Journal
DOI: 10.1021/jo015754q Document Type: Article

Times cited : (40)

References (105)

1
- 0034635169
- (2000) Biochemistry , vol.39 , pp. 117-126
- Vocadlo, D.J.¹ Mayer, C.² He, S.M.³ Withers, S.G.⁴

2
- 0033996047
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 1270-1277
- Namchuk, M.N.¹ McCarter, J.D.² Becalski, A.³ Andrews, T.⁴ Withers, S.G.⁵

3
- 0033435203
- (1999) Proc. Natl. Acad. Sci. U.S.A. , vol.96 , pp. 14270-14275
- Gu, X.R.¹ Liu, Y.Q.² Santi, D.V.³

4
- 0034674636
- (2000) Tetrahedron , vol.56 , pp. 4253-4260
- Michel, D.¹ Schlosser, M.²

5
- 0033230998
- (1999) Bioorg. Med. Chem. Lett. , vol.9 , pp. 3159-3164
- De Jonghe, S.¹ Van Overmeire, I.² Gunst, J.³ De Bruyn, A.⁴ Hendrix, C.⁵ Van Calenbergh, S.⁶ Busson, R.⁷ De Keukeleire, D.⁸ Philippe, J.⁹ Herdewijn, P.¹⁰

6
- 0032577017
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 3823-3835
- Gerfen, G.J.¹ Van der Donk, W.A.² Yu, G.X.³ McCarthy, J.R.⁴ Jarvi, E.T.⁵ Matthews, D.P.⁶ Farrar, C.⁷ Griffin, R.G.⁸ Stubbe, J.⁹

7
- 0030591846
- (1996) Bioorg. Med. Chem. Lett. , vol.6 , pp. 2967-2970
- Kim, D.H.¹ Park, J.I.²

8
- 0028074997
- (1994) Drug Metab. Rev. , vol.26 , pp. 605-643
- Park, B.K.¹ Kitteringham, N.R.²

9
- 0027432004
- (1993) Tetrahedron , vol.49 , pp. 9385-9445
- Resnati, G.¹

10
- 0027908693
- (1993) Carbohydr. Res. , vol.248 , pp. 143-150
- Egron, M.J.¹ LeClercq, F.² Antonakis, K.³ Bennanibaiti, M.I.⁴ Frayssinet, C.⁵

11
- 0026325216
- (1991) Biochemistry , vol.30 , pp. 10506-10512
- Dubois, J.¹ Dugave, C.² Foures, C.³ Kaminsky, M.⁴ Tabet, J.C.⁵ Bory, S.⁶ Gaudry, M.⁷ Marquet, A.⁸

12
- 0032947968
- (1999) Curr. Org. Chem. , vol.3 , pp. 287-307
- Dax, K.¹ Albert, M.² Ortner, J.³ Paul, B.J.⁴

13
- 0000836901
- (1996) Chem. Rev. , vol.96 , pp. 1557-1584
- Dolbier, W.R.¹

14
- 0000126155
- (1998) Angew. Chem., Int. Ed. Engl. , vol.37 , pp. 1497-1513
- Schlosser, M.¹

15
- 0003607570
- (1991) ACS Symp. Ser. , vol.456 , pp. 196-204
- Coward, J.K.¹ McGuire, J.J.² Galivan, J.³

16
- 0032486160
- (1998) Tetrahedron: Asymmetry , vol.9 , pp. 1989-1994
- Ito, H.¹ Saito, A.² Taguchi, T.³

17
- 0033593459
- (1999) J. Org. Chem. , vol.64 , pp. 540-546
- Tian, F.¹ Bartberger, M.D.² Dolbier, W.R.³

18
- 0344527830
- (1999) J. Org. Chem. , vol.64 , pp. 861-865
- Saunders, W.H.¹

19
- 0033529959
- (1999) J. Org. Chem. , vol.64 , pp. 5993-5999
- Li, A.R.¹ Shtarev, A.B.² Smart, B.E.³ Yang, Z.Y.⁴ Lusztyk, J.⁵ Ingold, K.U.⁶ Bravo, A.⁷ Dolbier, W.R.⁸

20
- 0000747582
- (2000) J. Comput. Chem. , vol.21 , pp. 426-431
- Headley, A.D.¹ Starnes, S.D.²

21
- 0033526306
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 4280-4281
- Barbarich, T.J.¹ Rithner, C.D.² Miller, S.M.³ Anderson, O.P.⁴ Strauss, S.H.⁵

22
- 0034175168
- (2000) J. Chem. Soc., Perkin Trans. 2 , pp. 605-607
- O'Hagan, D.¹ Bilton, C.² Howard, J.A.K.³ Knight, L.⁴ Tozer, D.J.⁵

23
- 1842663065
- (1997) Chem. Commun. , pp. 645-652
- O'Hagan, D.¹ Rzepa, H.S.²

24
- 0033541035
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 1912-1921
- Hoffmann, M.¹ Rychlewski, J.² Rychlewska, U.³

25
- 0002696051
- (1985) Heterocycles , vol.23 , pp. 45-49
- Tsushima, T.¹ Kawada, K.² Shiratori, O.³ Uchida, N.⁴

26
- 0030601896
- (1996) Biochem. Pharmacol. , vol.52 , pp. 1295-1303
- McGuire, J.J.¹ Hart, B.P.² Haile, W.H.³ Magee, K.J.⁴ Rhee, M.⁵ Bolanowska, W.E.⁶ Russell, C.⁷ Galivan, J.⁸ Paul, B.⁹ Coward, J.K.¹⁰

27
- 0030026396
- (1996) J. Med. Chem. , vol.39 , pp. 56-65
- Hart, B.P.¹ Haile, W.H.² Licato, N.J.³ Bolanowska, W.E.⁴ McGuire, J.J.⁵ Coward, J.K.⁶

28
- 0030052336
- (1996) J. Med. Chem. , vol.39 , pp. 66-72
- Tsukamoto, T.¹ Kitazume, T.² McGuire, J.J.³ Coward, J.K.⁴

29
- 0028978207
- (1995) Arch. Biochem. Biophys. , vol.321 , pp. 319-328
- McGuire, J.J.¹ Hart, B.P.² Haile, W.H.³ Rhee, M.S.⁴ Galivan, J.⁵ Coward, J.K.⁶

30
- 0031616927
- (1998) Adv. Enzymol. Relat. Areas Mol. Biol. , vol.72 , pp. 145-198
- Richards, N.G.J.¹ Schuster, S.M.²

31
- 0033534161
- (1999) Biochemistry , vol.38 , pp. 16146-16157
- Larsen, T.M.¹ Boehlein, S.K.² Schuster, S.M.³ Richards, N.G.J.⁴ Thoden, J.B.⁵ Holden, H.M.⁶ Rayment, I.⁷

32
- 0032558462
- (1998) Biochemistry , vol.37 , pp. 13230-13238
- Boehlein, S.K.¹ Stewart, J.D.² Walworth, E.S.³ Thirumoorthy, R.⁴ Richards, N.G.J.⁵ Schuster, S.M.⁶

33
- 0030014161
- (1996) J. Med. Chem. , vol.39 , pp. 2367-2378
- Parr, I.B.¹ Boehlein, S.K.² Dribben, A.B.³ Schuster, S.M.⁴ Richards, N.G.J.⁵

34
- 0027351423
- (1993) Adv. Enzymol. Relat. Areas Mol. Biol. , vol.66 , pp. 203-309
- Zalkin, H.¹

35
- 0031616926
- (1998) Adv. Enzymol. Relat. Areas Mol. Biol. , vol.72 , pp. 87-144
- Zalkin, H.¹ Smith, J.L.²

36
- 0015560566
- (1973) Adv. Enzymol. Relat. Areas Mol. Biol. , vol.39 , pp. 91-183
- Buchanan, J.M.¹

37
- 0025315269
- (1990) Nucl. Acids Res. , vol.18 , pp. 3509-3513
- Gong, S.S.¹ Basilico, C.L.²

38
- 0034282704
- (2000) J. Biol. Chem. , vol.275 , pp. 26976-26985
- Barbosa-Tessmann, I.P.¹ Chen, C.² Zhong, C.³ Siu, F.⁴ Schuster, S.M.⁵ Nick, H.S.⁶ Kilberg, M.S.⁷

39
- 0033615725
- (1999) J. Biol. Chem. , vol.274 , pp. 31139-31144
- Barbosa-Tessmann, I.P.¹ Chen, C.² Zhong, C.³ Schuster, S.M.⁴ Nick, H.S.⁵ Kilberg, M.S.⁶

40
- 0029969542
- (1996) J. Org. Chem. , vol.61 , pp. 2497-2500
- Tsukamoto, T.¹ Coward, J.K.²

41
- 0033619849
- (1999) Org. Lett. , vol.1 , pp. 2105-2107
- Konas, D.W.¹ Coward, J.K.²

42
- 0002226645
- (1990) Chem. Lett. , pp. 1307-1310
- Kitagawa, O.¹ Hashimoto, A.² Kobayashi, Y.³ Taguchi, T.⁴

43
- 0030052336
- (1996) J. Med. Chem. , vol.39 , pp. 66-72
- Tsukamoto, T.¹ Kitazume, T.² McGuire, J.J.³ Coward, J.K.⁴

44
- 0001523313
- (1993) J. Fluorine Chem. , vol.60 , pp. 193-210
- Hudlicky, M.¹

45
- 0026590329
- (1992) Tetrahedron Lett. , vol.33 , pp. 1509-1512
- Avent, A.G.¹ Bowler, A.N.² Doyle, P.M.³ Marchand, C.M.⁴ Young, D.W.⁵

46
- 0030749196
- (1997) Amino Acids , vol.12 , pp. 363-372
- Kroger, S.¹ Haufe, G.²

47
- 0025651962
- (1990) Tetrahedron Lett. , vol.31 , pp. 7403-7406
- Hudlicky, M.¹ Merola, J.S.²

48
- 0027164569
- (1993) Tetrahedron Lett. , vol.34 , pp. 4917-4920
- Hart, B.P.¹ Coward, J.K.²

49
- 0021715429
- (1984) Tetrahedron Lett. , vol.25 , pp. 4933-4936
- Taguchi, T.¹ Mitsuhashi, S.² Yamanouchi, A.³ Kobayashi, Y.⁴

50
- 0034353232
- (2000) Nat. Prod. Rep. , vol.17 , pp. 621-631
- Sutherland, A.¹ Willis, C.L.²

51
- 0032080830
- (1998) Bioorg. Med. Chem. Lett. , vol.8 , pp. 1097-1100
- Li, K.Q.¹ Leriche, C.² Liu, H.W.³

52
- 0032512020
- (1998) Tetrahedron , vol.54 , pp. 13887-13914
- Iseki, K.¹

53
- 0002838594
- (2000) J. Fluorine Chem. , vol.101 , pp. 11-14
- Tolman, V.¹ Sedmera, P.²

54
- 0001801308
- (2000) J. Fluorine Chem. , vol.101 , pp. 5-10
- Tolman, V.¹ Sedmera, P.²

55
- 0030561462
- (1996) Tetrahedron Asymm. , vol.7 , pp. 3545-3551
- Kokuryo, Y.¹ Nakatani, T.² Kobayashi, K.³ Tamura, Y.⁴ Kawada, K.⁵ Ohtani, M.⁶

56
- 0035906024
- (2001) Tetrahedron , vol.57 , pp. 1497-1507
- Rose, N.G.W.¹ Blaskovich, M.A.² Wong, A.³ Lajoie, G.A.⁴

57
- 0033607454
- (1999) J. Org. Chem. , vol.64 , pp. 8958-8961
- Rifé, J.¹ Ortuno, R.² Lajoie, G.A.³

58
- 0027236202
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 5021-5030
- Blaskovich, M.A.¹ Lajoie, G.A.²

59
- 0027300378
- (1993) Tetrahedron Lett. , vol.34 , pp. 3837-3840
- Blaskovich, M.A.¹ Lajoie, G.A.²

60
- 0002551083
- (1997) Top. Curr. Chem. , vol.193 , pp. 131-195
- Percy, J.M.¹

61
- 0029895833
- (1996) Tetrahedron , vol.52 , pp. 8619-8683
- Tozer, M.J.¹ Herpin, T.F.²

62
- 0003416163
- Kukhar', V. P., Soloshonok, V. A., Eds.; Wiley: Chichester
- (1995) Fluorine-Containing Amino Acids Synthesis and Properties

63
- 0023237559
- (1987) Tetrahedron , vol.43 , pp. 3123-3197
- Welch, J.T.¹

64
- 0027164569
- (1993) Tetrahedron Lett. , vol.34 , pp. 4917-4920
- Hart, B.P.¹ Coward, J.K.²

65
- 0021715429
- (1984) Tetrahedron Lett. , vol.25 , pp. 4933-4936
- Taguchi, T.¹ Mitsuhashi, S.² Yamanouchi, A.³ Kobayashi, Y.⁴

66
- 0034677688
- (2000) Chem. Eur. J. , vol.6 , pp. 1050-1063
- Vayron, P.¹ Renard, P.Y.² Valleix, A.³ Mioskowski, C.⁴

67
- 0001090596
- (1998) J. Org. Chem. , vol.63 , pp. 8052-8057
- Kotoris, C.C.¹ Chen, M.J.² Taylor, S.D.³

68
- 0029811418
- (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 1019-1021
- Nakano, T.¹ Makino, M.² Morizawa, Y.³ Matsumura, Y.⁴

69
- 33751156790
- (1995) J. Org. Chem. , vol.60 , pp. 4730-4737
- Davis, F.A.¹ Han, W.² Murphy, C.K.³

70
- 84988130722
- (1991) Synlett , pp. 187-189
- Differding, E.¹ Ofner, H.²

71
- 0003653038
- (1996) Synth. Commun. , vol.26 , pp. 4113-4122
- Benincasa, M.¹ Forti, L.² Ghelfi, F.³ Libertini, E.⁴ Pagnoni, U.M.⁵

72
- 0027043238
- (1992) J. Org. Chem. , vol.57 , pp. 7309-7314
- Robinson, R.P.¹ Donahue, K.M.²

73
- 0024519247
- (1989) J. Am. Chem. Soc. , vol.111 , pp. 3368-3374
- Takahashi, L.H.¹ Radhakrishnan, R.² Rosenfeld, R.E.³ Meyer, E.F.⁴ Trainor, D.A.⁵

74
- 0026716431
- (1992) Synthesis , pp. 565-570
- Chou, T.S.¹ Heath, P.C.² Paterson, L.E.³ Poteet, L.M.⁴ Lakin, R.E.⁵ Hunt, A.H.⁶

75
- 0033597918
- (1999) J. Org. Chem. , vol.64 , pp. 5599-5602
- Xu, Y.L.¹ Tian, F.² Dolbier, W.R.³

76
- 0001256768
- (1997) J. Org. Chem. , vol.62 , pp. 6503-6506
- Xu, Y.L.¹ Dolbier, W.R.²

77
- 0000827795
- (1997) J. Org. Chem. , vol.62 , pp. 1576-1577
- Xu, Y.L.¹ Dolbier, W.R.² Rong, X.X.³

78
- 0001460870
- (1989) J. Org. Chem. , vol.54 , pp. 3824-3831
- Lubell, W.¹ Rapoport, H.²

79
- 84986505884
- (1992) J. Comput. Chem. , vol.13 , pp. 214-228
- Guida, W.C.¹ Bohacek, R.S.² Erion, M.D.³

80
- 3042988525
- (1977) J. Am. Chem. Soc. , vol.99 , pp. 8127-8134
- Allinger, N.L.¹

81
- 84986437005
- (1990) J. Comput. Chem. , vol.11 , pp. 440-467
- Mohamadi, F.¹ Richards, N.G.J.² Guida, W.C.³ Liskamp, R.M.J.⁴ Lipton, M.A.⁵ Caufield, C.E.⁶ Chang, G.⁷ Hendrickson, T.⁸ Still, W.C.⁹

82
- 4344664124
- (1987) J. Am. Chem. Soc. , vol.109 , pp. 236-237
- Lubell, W.D.¹ Rapoport, H.²

83
- 0025025831
- (1990) J. Org. Chem. , vol.55 , pp. 3511-3522
- Lubell, W.D.¹ Jamison, T.F.² Rapoport, H.³

84
- 33845283518
- (1987) J. Org. Chem. , vol.52 , pp. 5486-5487
- Cha, J.¹ Kwon, S.S.²

85
- 0003527811
- note

86
- 0001399730
- (1980) Top. Curr. Chem. , vol.88 , pp. 145-163
- Anh, N.T.¹

87
- 49149146087
- (1980) Tetrahedron , vol.36 , pp. 2-72
- Bartlett, P.A.¹

88
- 0034615896
- (2000) J. Org. Chem. , vol.65 , pp. 2134-2137
- Xu, Y.L.¹ Dolbier, W.R.²

89
- 0032506573
- (1998) Tetrahedron Lett. , vol.39 , pp. 9151-9154
- Xu, Y.L.¹ Dolbier, W.R.²

90
- 0027300378
- (1993) Tetrahedron Lett. , vol.34 , pp. 3837-3840
- Blaskovich, M.A.¹ Lajoie, G.A.²

91
- 0027359371
- (1993) Tetrahedron Lett. , vol.34 , pp. 7195-7196
- Kim, K.S.¹ Qian, L.²

92
- 85080848604
- (1998) Angew. Chem., Int. Ed. Engl. , vol.37 , pp. 3073-3082
- Baguley, P.A.¹ Walton, J.C.²

93
- 0002436598
- (1997) Top. Curr. Chem. , vol.192 , pp. 97-163
- Dolbier, W.R.¹

94
- 0034096656
- (2000) Nucleosides Nucleotides , vol.19 , pp. 1-12
- Siddiqui, M.A.¹ Driscoll, J.S.² Abushanab, E.³ Kelley, J.A.⁴ Barchi, J.J.⁵ Marquez, V.E.⁶

95
- 0344902741
- (1975) J. Chem. Soc., Perkin Trans. 1 , pp. 1574-1585
- Barton, D.H.R.¹ McCombie, S.W.²

96
- 0000697108
- (1997) Chem. Rev. , vol.97 , pp. 3273-3312
- Beckwith, A.L.J.¹ Crich, D.² Duggan, P.J.³ Yao, Q.W.⁴

97
- 0027479919
- (1993) Tetrahedron , vol.49 , pp. 2793-2804
- Barton, D.H.R.¹ Jang, D.O.² Jaszberenyi, J.C.³

98
- 0026738595
- (1992) Tetrahedron , vol.48 , pp. 7435-7446
- Barton, D.H.R.¹ Dorchak, J.² Jaszberenyi, J.C.³

99
- 0026607504
- (1992) Tetrahedron , vol.48 , pp. 2529-2544
- Barton, D.H.R.¹

100
- 0001392622
- (1998) J. Org. Chem. , vol.63 , pp. 3631-3646
- Blaskovich, M.A.¹ Evindar, G.² Rose, N.G.W.³ Wilkinson, S.⁴ Luo, Y.⁵ Lajoie, G.A.⁶

101
- 0001186144
- (1983) Tetrahedron Lett. , vol.24 , pp. 5571-5574
- Corey, E.J.¹ Raju, N.²

102
- 0003527815
- note

103
- 0025984290
- (1991) Tetrahedron Lett. , vol.32 , pp. 7187-7190
- Barton, D.H.R.¹ Jang, D.O.² Jaszberenyi, J.C.³

104
- 0002714675
- (1978) J. Org. Chem. , vol.43 , pp. 2923-2935
- Still, W.C.¹ Kahn, M.² Mitra, A.³

105
- 0004150157
- Bruker-AXS: Madison, WI
- (1998) SHELXTL5
- Sheldrick, G.M.¹

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