3.11 Creation and Optimization of Artificial Enzymes for Abiological Reactions

R. Obexer; X. Garrabou; D. Hilvert

doi:10.1055/sos-SD-216-00397

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Faber, K. et al.: 2015 Science of Synthesis: Biocatalysis in Organic Synthesis 3 DOI: 10.1055/sos-SD-216-00397

Biocatalysis in Organic Synthesis 3

3.11 Creation and Optimization of Artificial Enzymes for Abiological Reactions

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Editors: Faber, K.; Fessner, W.-D.; Turner, N. J.

Authors: Allen, C. C. R.; de Gonzalo, G.; Ellinger, J. J.; Ewing, T. A.; Faber, K.; Fernández-Lucas, J.; Flynn, C. M.; Fraaije, M. W.; García-Junceda, E.; Garrabou, X.; Gkotsi, D. S.; Glueck, S. M.; Goss, R. J. M.; Grogan, G.; Gröger, H.; Grüschow, S.; Hammer, S. C.; Hauer, B.; Herter, S.; Hilvert, D.; Hollmann, F.; Hormigo, D.; Hummel, W.; Molla, G.; Nestl, B. M.; Nolte, J. C.; Obexer, R.; Oroz-Guinea, I.; Patel, R. N.; Pollegioni, L.; Quin, M. B.; Schmidt-Dannert, C.; Smith, D. R. M.; Turner, N. J.; Urlacher, V. B.; van Berkel, W. J. H.; Woodley, J. M.

Title: Biocatalysis in Organic Synthesis 3

Print ISBN: 9783131746610; Online ISBN: 9783131974914; Book DOI: 10.1055/b-003-125814

1st edition © 2015. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Subjects: Organic Chemistry

Science of Synthesis Reference Libraries

Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Type: Multivolume Edition

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Abstract

Catalytic antibody technology and computational design represent conceptually distinct strategies to artificial enzymes. Both approaches provide significant activities and tailored specificities for mechanistically distinct transformations, including abiological and asymmetric reactions. This review compares the relative strengths and limitations of such de novo catalysts, delineating challenges to overcome in the pursuit of synthetically useful enzymes for any given chemical transformation.

Key words

catalytic antibodies - computational design - directed evolution - Diels–Alder reaction - Kemp elimination - (retro-)aldol reaction - ester hydrolysis - metalloenzymes - computational redesign

1 Schmid A, Dordick JS, Hauer B, Kiener A, Wubbolts M, Witholt B. Nature (London) 2001; 409: 258

Search in Google Scholar

2 Bornscheuer UT, Huisman GW, Kazlauskas RJ, Lutz S, Moore JC, Robins K. Nature (London) 2012; 485: 185

Search in Google Scholar

3 Koeller KM, Wong C.-H. Nature (London) 2001; 409: 232

Search in Google Scholar

4 Schoemaker HE, Mink D, Wubbolts MG. Science (Washington, D. C.) 2003; 299: 1694

PubMed Search in Google Scholar

5 Chen W, Brühlmann F, Richins RD, Mulchandani A. Curr. Opin. Biotechnol. 1999; 10: 137

PubMed Search in Google Scholar

6 Ang EL, Zhao H, Obbard JP. Enzyme Microb. Technol. 2005; 37: 487

Search in Google Scholar

7 Bethune MT, Khosla C. Methods Enzymol. 2012; 502: 241

Search in Google Scholar

8 Hershfield MS, Buckley RH, Greenberg ML, Melton AL, Schiff R, Hatem C, Kurtzberg J, Markert ML, Kobayashi RH, Kobayashi AL, Abuchowski A. N. Engl. J. Med. 1987; 316: 589

PubMed Search in Google Scholar

9 Kopetzki E, Lehnert K, Buckel P. Clin. Chem. (Washington, DC, U. S.) 1994; 40: 688

PubMed Search in Google Scholar

10 Polizzi KM, Bommarius AS, Broering JM, Chaparro-Riggers JF. Curr. Opin. Chem. Biol. 2007; 11: 220

PubMed Search in Google Scholar

11 Jäckel C, Kast P, Hilvert D. Annu. Rev. Biophys. 2008; 37: 153

PubMed Search in Google Scholar

12 Romero PA, Arnold FH. Nature Rev. Mol. Cell Biol. 2009; 10: 866

PubMed Search in Google Scholar

13 Bornscheuer UT, Pohl M. Curr. Opin. Chem. Biol. 2001; 5: 137

PubMed Search in Google Scholar

14 Reetz MT, Jaeger K.-E. Chem.–Eur. J. 2000; 6: 407

PubMed Search in Google Scholar

15 Reetz MT. Proc. Natl. Acad. Sci. U. S. A. 2004; 101: 5716

PubMed Search in Google Scholar

16 Turner NJ. Trends Biotechnol. 2003; 21: 474

PubMed Search in Google Scholar

17 Savile CK, Janey JM, Mundorff EC, Moore JC, Tam S, Jarvis WR, Colbeck JC, Krebber A, Fleitz FJ, Brands J, Devine PN, Huisman GW, Hughes GJ. Science (Washington, D. C.) 2010; 329: 305

PubMed Search in Google Scholar

18 Aharoni A, Gaidukov L, Khersonsky O, Gould SM, Roodveldt C, Tawfik DS. Nature Genet. 2005; 37: 73

PubMed Search in Google Scholar

19 Babtie A, Tokuriki N, Hollfelder F. Curr. Opin. Chem. Biol. 2010; 14: 200

PubMed Search in Google Scholar

20 Kazlauskas RJ. Curr. Opin. Chem. Biol. 2005; 9: 195

PubMed Search in Google Scholar

21 Cadwell RC, Joyce GF. Genome Res. 1994; 3: S136

Search in Google Scholar

22 Wells JA, Vasser M, Powers DB. Gene 1985; 34: 315

PubMed Search in Google Scholar

23 Stemmer WPC. Nature (London) 1994; 370: 389

Search in Google Scholar

24 Gupta RD, Tawfik DS. Nature Methods 2008; 5: 939

PubMed Search in Google Scholar

25 Bloom JD, Romero PA, Lu Z, Arnold FH. Biol. Direct 2007; 2: 17

PubMed Search in Google Scholar

26 Chen Z, Zhao H. J. Mol. Biol. 2005; 348: 1273

PubMed Search in Google Scholar

27 Pauling L. Chem. Eng. News 1946; 24: 1375

Search in Google Scholar

28 Jencks WP. Catalysis in Chemistry and Enzymology. McGraw-Hill; New York 1969

Search in Google Scholar

29 Hilvert D. Annu. Rev. Biochem. 2000; 69: 751

PubMed Search in Google Scholar

30 Hilvert D. Top. Stereochem. 1999; 22: 83

Search in Google Scholar

31 Janda KD, Shevlin CG, Lerner RA. Science (Washington, D. C.) 1993; 259: 490

PubMed Search in Google Scholar

32 Radzicka A, Wolfenden R. Science (Washington, D. C.) 1995; 267: 90

PubMed Search in Google Scholar

33 Edwards DR, Lohman DC, Wolfenden R. J. Am. Chem. Soc. 2012; 134: 525

PubMed Search in Google Scholar

34 Takahashi N, Kakinuma H, Liu L, Nishi Y, Fujii I. Nature Biotechnol. 2001; 19: 563

PubMed Search in Google Scholar

35 Tao H, Cornish VW. Curr. Opin. Chem. Biol. 2002; 6: 858

PubMed Search in Google Scholar

36 Piran R, Keinan E, Catalytic Antibodies. Keinan E. Wiley-VCH; Weinheim, Germany 2005: 243

Crossref Search in Google Scholar

37 Kries H, Blomberg R, Hilvert D. Curr. Opin. Chem. Biol. 2013; 17: 221

PubMed Search in Google Scholar

38 Kiss G, Çelebi-Ölçüm N, Moretti R, Baker D, Houk KN. Angew. Chem. 2013; 125: 5810 Angew. Chem. Int. Ed. 2013; 52: 5700

PubMed Search in Google Scholar

39 Hilvert D. Annu. Rev. Biochem. 2013; 82: 447

PubMed Search in Google Scholar

40 Tantillo DJ, Chen J, Houk KN. Curr. Opin. Chem. Biol. 1998; 2: 743

PubMed Search in Google Scholar

41 Zanghellini A, Jiang L, Wollacott AM, Cheng G, Meiler J, Althoff EA, Röthlisberger D, Baker D. Protein Sci. 2006; 15: 2785

PubMed Search in Google Scholar

42 Bolon DN, Mayo SL. Proc. Natl. Acad. Sci. U. S. A. 2001; 98: 14274

PubMed Search in Google Scholar

43 Malisi C, Kohlbacher O, Höcker B. Proteins: Struct., Funct., Bioinf. 2009; 77: 74

PubMed Search in Google Scholar

44 Lassila JK, Privett HK, Allen BD, Mayo SL. Proc. Natl. Acad. Sci. U. S. A. 2006; 103: 16710

PubMed Search in Google Scholar

45 Meiler J, Baker D. Proteins: Struct., Funct., Bioinf. 2006; 65: 538

PubMed Search in Google Scholar

46 Schmidt RR. Acc. Chem. Res. 1986; 19: 250

Search in Google Scholar

47 Juhl M, Tanner D. Chem. Soc. Rev. 2009; 38: 2983

PubMed Search in Google Scholar

48 Katayama K, Kobayashi T, Oikawa H, Honma M, Ichihara A. Biochim. Biophys. Acta, Protein Struct. Mol. Enzymol. 1998; 1384: 387

PubMed Search in Google Scholar

49 Auclair K, Sutherland A, Kennedy J, Witter DJ, Van den Heever JP, Hutchinson CR, Vederas JC. J. Am. Chem. Soc. 2000; 122: 11519

Search in Google Scholar

50 Stocking EM, Williams RM. Angew. Chem. 2003; 115: 3186 Angew. Chem. Int. Ed. 2003; 42: 3078

PubMed Search in Google Scholar

51 Kim HJ, Ruszczycky MW, Choi S, Liu Y, Liu H. Nature (London) 2011; 473: 109

Search in Google Scholar

52 Hilvert D, Hill KW, Nared KD, Auditor M.-TM. J. Am. Chem. Soc. 1989; 111: 9261

Search in Google Scholar

53 Xu J, Deng Q, Chen J, Houk KN, Bartek J, Hilvert D, Wilson IA. Science (Washington, D. C.) 1999; 286: 2345

PubMed Search in Google Scholar

54 Kirby AJ. Adv. Phys. Org. Chem. 1981; 17: 183

Search in Google Scholar

55 Braisted AC, Schultz PG. J. Am. Chem. Soc. 1990; 112: 7430

Search in Google Scholar

56 Zhang X, Deng Q, Yoo SH, Houk KN. J. Org. Chem. 2002; 67: 9043

PubMed Search in Google Scholar

57 Romesberg FE, Schultz PG. Bioorg. Med. Chem. Lett. 1999; 9: 1741

Search in Google Scholar

58 Gouverneur VE, Houk KN, de Pascual-Teresa B, Beno B, Janda KD, Lerner RA. Science (Washington, D. C.) 1993; 262: 204

PubMed Search in Google Scholar

59 Siegel JB, Zanghellini A, Lovick HM, Kiss G, Lambert AR, St.Clair JL, Gallaher JL, Hilvert D, Gelb MH, Stoddard BL, Houk KN, Michael FE, Baker D. Science (Washington, D. C.) 2010; 329: 309

PubMed Search in Google Scholar

60 Yli-Kauhaluoma JT, Ashley JA, Lo C.-H, Tucker L, Wolfe MM, Janda KD. J. Am. Chem. Soc. 1995; 117: 7041

Search in Google Scholar

61 Eiben CB, Siegel JB, Bale JB, Cooper S, Khatib F, Shen BW, Players F, Stoddard BL, Popovic Z, Baker D. Nature Biotechnol. 2012; 30: 190

PubMed Search in Google Scholar

62 Preiswerk N, Beck T, Schulz JD, Milovnik P, Mayer C, Siegel JB, Baker D, Hilvert D. Proc. Natl. Acad. Sci. U. S. A. 2014; 111: 8013

PubMed Search in Google Scholar

63 Birney DM, Houk KN. J. Am. Chem. Soc. 1990; 112: 4127

Search in Google Scholar

64 Evans DA, Miller SJ, Lectka T, Von Matt P. J. Am. Chem. Soc. 1999; 121: 7559

Search in Google Scholar

65 Kündig EP, Saudan CM, Bernardinelli G. Angew. Chem. 1999; 111: 1297 Angew. Chem. Int. Ed. 1999; 38: 1220

Search in Google Scholar

66 Ishitani H, Kobayashi S. Tetrahedron Lett. 1996; 37: 7357

Search in Google Scholar

67 Casey ML, Kemp DS, Paul KG, Cox DD. J. Org. Chem. 1973; 38: 2294

Search in Google Scholar

68 Kemp DS. J. Am. Chem. Soc. 1973; 95: 6670

Search in Google Scholar

69 Kemp DS, Cox DD, Paul KG. J. Am. Chem. Soc. 1975; 97: 7312

Search in Google Scholar

70 Thorn SN, Daniels RG, Auditor M.-TM, Hilvert D. Nature (London) 1995; 373: 228

Search in Google Scholar

71 Debler EW, Ito S, Seebeck FP, Heine A, Hilvert D, Wilson IA. Proc. Natl. Acad. Sci. U. S. A. 2005; 102: 4984

PubMed Search in Google Scholar

72 Albery WJ, Knowles JR. Biochemistry 1976; 15: 5627

Search in Google Scholar

73 Korendovych IV, Kulp DW, Wu Y, Cheng H, Roder H, DeGrado WF. Proc. Natl. Acad. Sci. U. S. A. 2011; 108: 6823

PubMed Search in Google Scholar

74 Moroz OV, Moroz YS, Wu Y, Olsen AB, Cheng H, Mack KL, McLaughlin JM, Raymond EA, Zhezherya K, Roder H, Korendovych IV. Angew. Chem. 2013; 125: 6366 Angew. Chem. Int. Ed. 2013; 52: 6246

PubMed Search in Google Scholar

75 Röthlisberger D, Khersonsky O, Wollacott AM, Jiang L, DeChancie J, Betker J, Gallaher JL, Althoff EA, Zanghellini A, Dym O, Albeck S, Houk KN, Tawfik DS, Baker D. Nature (London) 2008; 453: 190

Search in Google Scholar

76 Khersonsky O, Röthlisberger D, Dym O, Albeck S, Jackson CJ, Baker D, Tawfik DS. J. Mol. Biol. 2010; 396: 1025

PubMed Search in Google Scholar

77 Khersonsky O, Röthlisberger D, Wollacott AM, Murphy P, Dym O, Albeck S, Kiss G, Houk KN, Baker D, Tawfik DS. J. Mol. Biol. 2011; 407: 391

PubMed Search in Google Scholar

78 Khersonsky O, Kiss G, Röthlisberger D, Dym O, Albeck S, Houk KN, Baker D, Tawfik DS. Proc. Natl. Acad. Sci. U. S. A. 2012; 109: 10358

PubMed Search in Google Scholar

79 Privett HK, Kiss G, Lee TM, Blomberg R, Chica RA, Thomas LM, Hilvert D, Houk KN, Mayo SL. Proc. Natl. Acad. Sci. U. S. A. 2012; 109: 3790

PubMed Search in Google Scholar

80 Blomberg R, Kries H, Pinkas DM, Mittl PRE, Grütter MG, Privett HK, Mayo SL, Hilvert D. Nature (London) 2013; 503: 418

Search in Google Scholar

81 Mukherjee S, Yang JW, Hoffmann S, List B. Chem. Rev. 2007; 107: 5471

PubMed Search in Google Scholar

82 Müller MM, Windsor MA, Pomerantz WC, Gellman SH, Hilvert D. Angew. Chem. 2009; 121: 940 Angew. Chem. Int. Ed. 2009; 48: 922

PubMed Search in Google Scholar

83 Tanaka F, Fuller R, Barbas III CF. Biochemistry 2005; 44: 7583

Search in Google Scholar

84 Gefflaut T, Blonski C, Perie J, Willson M. Prog. Biophys. Mol. Biol. 1995; 63: 301

PubMed Search in Google Scholar

85 Wagner J, Lerner RA, Barbas III CF. Science (Washington, D. C.) 1995; 270: 1797

PubMed Search in Google Scholar

86 Zhong G, Lerner RA, Barbas III CF. Angew. Chem. 1999; 111: 3957 Angew. Chem. Int. Ed. 1999; 38: 3738

PubMed Search in Google Scholar

87 Barbas III CF, Heine A, Zhong G, Hoffmann T, Gramatikova S, Björnestedt R, List B, Anderson J, Stura EA, Wilson IA, Lerner RA. Science (Washington, D. C.) 1997; 278: 2085

PubMed Search in Google Scholar

88 Zhu X, Tanaka F, Lerner RA, Barbas III CF, Wilson IA. J. Am. Chem. Soc. 2009; 131: 18206

PubMed Search in Google Scholar

89 Hoffmann T, Zhong G, List B, Shabat D, Anderson J, Gramatikova S, Lerner RA, Barbas III CF. J. Am. Chem. Soc. 1998; 120: 2768

Search in Google Scholar

90 List B, Shabat D, Barbas III CF, Lerner RA. Chem.–Eur. J. 1998; 4: 881

Search in Google Scholar

91 Sinha SC, Barbas III CF, Lerner RA. Proc. Natl. Acad. Sci. U. S. A. 1998; 95: 14603

PubMed Search in Google Scholar

92 Shabat D, Rader C, List B, Lerner RA, Barbas III CF. Proc. Natl. Acad. Sci. U. S. A. 1999; 96: 6925

PubMed Search in Google Scholar

93 Rader C, Sinha SC, Popkov M, Lerner RA, Barbas III CF. Proc. Natl. Acad. Sci. U. S. A. 2003; 100: 5396

PubMed Search in Google Scholar

94 Jiang L, Althoff EA, Clemente FR, Doyle L, Röthlisberger D, Zanghellini A, Gallaher JL, Betker JL, Tanaka F, Barbas III CF, Hilvert D, Houk KN, Stoddard BL, Baker D. Science (Washington, D. C.) 2008; 319: 1387

PubMed Search in Google Scholar

95 Althoff EA, Wang L, Jiang L, Giger L, Lassila JK, Wang Z, Smith M, Hari S, Kast P, Herschlag D, Hilvert D, Baker D. Protein Sci. 2012; 21: 717

PubMed Search in Google Scholar

96 Lassila JK, Baker D, Herschlag D. Proc. Natl. Acad. Sci. U. S. A. 2010; 107: 4937

PubMed Search in Google Scholar

97 Giger L, Caner S, Obexer R, Kast P, Baker D, Ban N, Hilvert D. Nature Chem. Biol. 2013; 9: 494

PubMed Search in Google Scholar

98 Wang L, Althoff EA, Bolduc J, Jiang L, Moody J, Lassila JK, Giger L, Hilvert D, Stoddard B, Baker D. J. Mol. Biol. 2012; 415: 615

PubMed Search in Google Scholar

99 Obexer R, Studer S, Giger L, Pinkas DM, Grütter MG, Baker D, Hilvert D. ChemCatChem 2014; 6: 1043

Search in Google Scholar

100 Bjelic S, Kipnis Y, Wang L, Pianowski Z, Vorobiev S, Su M, Seetharaman J, Xiao R, Kornhaber G, Hunt JF, Tong L, Hilvert D, Baker D. J. Mol. Biol. 2014; 426: 256

PubMed Search in Google Scholar

101 Jaeger K.-E, Eggert T. Curr. Opin. Biotechnol. 2002; 13: 390

PubMed Search in Google Scholar

102 Jackson DY, Burnier J, Quan C, Stanley M, Tom J, Wells JA. Science (Washington, D. C.) 1994; 266: 243

PubMed Search in Google Scholar

103 Bordusa F. Chem. Rev. 2002; 102: 4817

PubMed Search in Google Scholar

104 Stewart JD, Liotta LJ, Benkovic SJ. Acc. Chem. Res. 1993; 26: 396

Search in Google Scholar

105 Janda KD, Benkovic SJ, Lerner RA. Science (Washington, D. C.) 1989; 244: 437

PubMed Search in Google Scholar

106 Janda KD, Schloeder D, Benkovic SJ, Lerner RA. Science (Washington, D. C.) 1988; 241: 1188

PubMed Search in Google Scholar

107 Benkovic SJ, Adams JA, Borders Jr CL, Janda KD, Lerner RA. Science (Washington, D. C.) 1990; 250: 1135

PubMed Search in Google Scholar

108 Stewart JD, Krebs JF, Siuzdak G, Berdis AJ, Smithrud DB, Benkovic SJ. Proc. Natl. Acad. Sci. U. S. A. 1994; 91: 7404

PubMed Search in Google Scholar

109 Kirsch JF, Jencks WP. J. Am. Chem. Soc. 1964; 86: 833

Search in Google Scholar

110 Richter F, Blomberg R, Khare SD, Kiss G, Kuzin AP, Smith AJT, Gallaher J, Pianowski Z, Helgeson RC, Grjasnow A, Xiao R, Seetharaman J, Su M, Vorobiev S, Lew S, Forouhar F, Kornhaber GJ, Hunt JF, Montelione GT, Tong L, Houk KN, Hilvert D, Baker D. J. Am. Chem. Soc. 2012; 134: 16197

PubMed Search in Google Scholar

111 Gerlt JA, Babbitt PC. Annu. Rev. Biochem. 2001; 70: 209

PubMed Search in Google Scholar

112 Gordon SR, Stanley EJ, Wolf S, Toland A, Wu SJ, Hadidi D, Mills JH, Baker D, Pultz IS, Siegel JB. J. Am. Chem. Soc. 2012; 134: 20513

PubMed Search in Google Scholar

113 Petrik ID, Liu J, Lu Y. Curr. Opin. Chem. Biol. 2014; 19: 67

PubMed Search in Google Scholar

114 Zastrow ML, Peacock FA, Stuckey JA, Pecoraro VL. Nature Chem. 2012; 4: 118

Search in Google Scholar

115 Kaplan J, DeGrado WF. Proc. Natl. Acad. Sci. U. S. A. 2004; 101: 11566

PubMed Search in Google Scholar

116 Chen Z, Vohidov F, Coughlin JM, Stagg LJ, Arold ST, Ladbury JE, Ball ZT. J. Am. Chem. Soc. 2012; 134: 10138

PubMed Search in Google Scholar

117 Der BS, Edwards DR, Kuhlman B. Biochemistry 2012; 51: 3933

Search in Google Scholar

118 Murphy PM, Bolduc JM, Gallaher JL, Stoddard BL, Baker D. Proc. Natl. Acad. Sci. U. S. A. 2009; 106: 9215

PubMed Search in Google Scholar

119 Khare SD, Kipnis Y, Greisen PJ, Takeuchi R, Ashani Y, Goldsmith M, Song Y, Gallaher JL, Silman I, Leader H, Sussman JL, Stoddard BL, Tawfik DS, Baker D. Nature Chem. Biol. 2012; 8: 294

PubMed Search in Google Scholar

120 Lazaridis T, Karplus M. Proteins: Struct., Funct., Genet. 1999; 35: 133

PubMed Search in Google Scholar

121 Acevedo O, Jorgensen WL. Acc. Chem. Res. 2010; 43: 142

PubMed Search in Google Scholar

122 Alexandrova AN, Röthlisberger D, Baker D, Jorgensen WL. J. Am. Chem. Soc. 2008; 130: 15907

PubMed Search in Google Scholar

123 Ruscio JZ, Kohn JE, Ball KA, Head-Gordon T. J. Am. Chem. Soc. 2009; 131: 14111

PubMed Search in Google Scholar

124 Frushicheva MP, Cao J, Chu ZT, Warshel A. Proc. Natl. Acad. Sci. U. S. A. 2010; 107: 16869

PubMed Search in Google Scholar

125 Kiss G, Röthlisberger D, Baker D, Houk KN. Protein Sci. 2010; 19: 1760

PubMed Search in Google Scholar

126 Kipnis Y, Baker D. Protein Sci. 2012; 21: 1388

PubMed Search in Google Scholar

127 Gerlt JA, Raushel FM. Curr. Opin. Chem. Biol. 2003; 7: 252

PubMed Search in Google Scholar

128 Höcker B, Jürgens C, Wilmanns M, Sterner R. Curr. Opin. Biotechnol. 2001; 12: 376

PubMed Search in Google Scholar

129 Mills JH, Khare SD, Bolduc JM, Forouhar F, Mulligan VK, Lew S, Seetharaman J, Tong L, Stoddard BL, Baker D. J. Am. Chem. Soc. 2013; 135: 13393

PubMed Search in Google Scholar