Bioinspired chemical inversion of L-amino acids to D-amino acids

Journal of the American Chemical Society

Volumn 129, Issue 6, 2007, Pages 1518-1519

  Park, Hyunjung ^a   Kwan, Mook Kim ^a   Lee, Areum ^b   Ham, Sihyun ^b   Nam, Wonwoo ^a   Chin, Jik ^c  

^a Ewha Womans University   (South Korea)

^b Sookmyung Women's University   (South Korea)

^c UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

2 OXOACID; ALANINE; ALPHA AMINO ACID; AMINO ACID; ARGININE; ASPARAGINE; DEXTRO AMINO ACID; GLUTAMIC ACID; GLUTAMINE; HISTIDINE; IMINE; LEUCINE; METHIONINE; PHENYLALANINE; PYRIDOXAL; PYRIDOXAL 5 PHOSPHATE; PYRIDOXAMINE; SERINE; THREONINE; TRYPTOPHAN; TYROSINE;

AMINO ACID ANALYSIS; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; EPIMERIZATION; HYDROGEN BOND; INTERNAL RESONANCE ASSISTED HYDROGEN BOND; NEUROTRANSMISSION; PROTON NUCLEAR MAGNETIC RESONANCE; RECEPTOR BINDING; STEREOCHEMISTRY;

AMINO ACIDS; IMINES; KINETICS; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; STEREOISOMERISM;

EID: 33847000255     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja067724g     Document Type: Article

References (36)

1. (a) Kreil, G. Science 1994, 266, 996-997.
2. (b) Corrigan, J. J. Science 1969, 164, 142-149.
3. (a) Wolosker, H.; Blackshaw, S.; Snyder, S. H. Proc. Nat. Acad. Sci. U.S.A. 1999, 96, 13409-13414.
4. (b) Wickelgren, I. Science 1999, 286, 1265-1266.
5. (c) Fujii, K.; Maedal, K.; Hikida, T.; Mustafa, A. K.; Balkissoon, R.; Xia, J.; Yamada, T.; Ozekil, Y.; Kawahara, R.; Okawa, M.; Huganir, R. L.; Ujike, H.; Snyder, S. H.; Sawa, A. Mol. Psychiatry 2006, 11, 150-157.
6. Stryer, L. Biochemistry, 4th ed.; W. H. Freeman and Co.: New York, 2000; pp 201-202.
7. (a) Shaw, J. P.; Petsko, G. A. Ringe, D. Biochemistry 1997, 36, 1329-1342.
8. (b) Walsh, C. T. J. Biol. Chem. 1989, 264, 2393-2396.
9. (a) Gilli, P.; Bertolasi, V.; Ferretti, V.; Gilli, G. J. Am. Chem. Soc. 2000, 122, 10405-10417.
10. (b) Kim, H.-J.; Kim, W.; Lough, A. J.; Kim, B. M.; Chin, J. J. Am. Chem. Soc. 2005, 127, 16776-16777.
11. (c) Kim, H.-J.; Kim, H.; Alhakimi, G.; Jeong, E. J.; Thavarajah, N.; Studnicki, L.; Koprianiuk, A.; Lough, A. J.; Suh, J.; Chin, J. J. Am. Chem. Soc. 2005, 127, 16370-16371.
12. Kim, K. M.; Park, H.; Kim, H.-J.; Chin, J.; Nam, W. Org. Lett. 2005, 7, 3525-3527.
13. Meca, L.; Reha, D.; Havlas, Z. J. Org. Chem. 2003, 68, 5677-5680.
14. Some limitations for the other six amino acids are given in the Supporting Information.
15. (a) Newcomb, M.; Toner, J. L.; Helgeson, R. C.; Cram, D. J. J. Am. Chem. Soc. 1979, 101, 4941-4947,
16. (b) Zhang, X. X.; Bradshaw, J. S.; Izatt, R. M. Chem. Rev. 1997, 97, 3313-3361.
17. (c) Breccia, P.; Van Gool, M.; Perez-Fernandez, R.; Martin-Santamaria, S.; Gago, F.; Prados, P.; Mendoza, J. J. Am. Chem. Soc. 2003, 125, 8270-8284.
18. (d) Oliva, A. I.; Simon, L.; Hernandez, J. V.; Muniz, F. M.; Lithgow, A.; Jimenez, A.; Moran, J. R. J. Chem. Soc., Perkin Trans. 2 2002, 1050-1052.
19. (e) Pazicky, M.; Gaspar, B.; Solladie-Cavallo, A.; Salisova, M.; Bohac, A.; Hutta, M.; Addova, G. Synthesis 2006, 12, 2013-2018.
20. (a) Famulok, M. Science 1996, 272, 1343-1346.
21. (b) Hofstetter, O.; Hofstetter, H.; Schurig, V.; Wilchek, M.; Green, B. S. J. Am. Chem. Soc. 1998, 120, 3251-3252.
22. (a) Osawa, T.; Shirasaka, K.; Matsui, T.; Yoshihara, S.; Akiyama, T.; Hishiya, T.; Asanuma, H.; Komiyama, M. Macromolecules 2006, 39, 2460-2466.
23. (b) Okuno, H.; Kitano, T.; Yakabe, H.; Kishimoto, M.; Deore, B. A.; Siigi, H.; Nagaoka, T. Anal. Chem. 2002, 74, 4184-4190.
24. (a) Job, R. C.; Bruice, T. J. Am. Chem. Soc. 1974, 96, 809-819.
25. (b) Chin, J.; Lee, S. S.; Lee, K. J.; Park, S.; Kim, D. H. Nature 1999, 401, 254-257.
26. (c) Reeve, T. B.; Cros, J.-P.; Gennari, C.; Piarulli, U.; Vries, J. G. Angew. Chem., Int. Ed. 2006, 118, 2509-2513.
27. See Supporting Information.
28. Chin, J.; Kim, D. C.; Kim, H.-J.; Panosyan, F. B.; Kim, K. M. Org. Lett. 2004, 6, 2591-2593.
29. Turner, N. J. Curr. Opin. Chem. Biol. 2004, 8, 114-119.
30. Gaussian 03 was used for the geometry optimizations (DFT at the B3LYP/ 6-31* level). (a) Kohn, W.; Sham, L. J. Phys. Rev. 1965, 140, A1133-1138.
31. (b) Gill, P. M. W.; Johnson, B. G.; Pople, J. A. Chem. Phys. Lett. 1993, 209, 506-512.
32. (c) Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
33. (d) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B: Condens. Matter Mater. Phys. 1988, 37, 785-789.
34. Kumar, G. A.; McAllister, M. A. J. Org. Chem. 1998, 63, 6968-8972.
35. (a) Breslow, R. Acc. Chem. Res. 1995, 28, 146-153.
36. (b) Liu, L.; Zhou, W.; Chruma, J.; Breslow, R. J. Am. Chem. Soc. 2004, 126, 8136-8137.