Telescopic one-pot condensation-hydroamination strategy for the synthesis of optically pure L-phenylalanines from benzaldehydes

Tetrahedron

Volumn 72, Issue 46, 2016, Pages 7256-7262

  Parmeggiani, Fabio ^a   Ahmed, Syed T ^a   Weise, Nicholas J ^a   Turner, Nicholas J ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

Amino acids; Ammonia lyases; Biocatalysis; Chemo enzymatic synthesis; Enantioselective catalysis; Microwave assisted synthesis

Indexed keywords

AMMONIA; BENZALDEHYDE DERIVATIVE; PHENYLALANINE AMMONIA LYASE; PHENYLALANINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; BIOCATALYSIS; BIOCATALYST; CHEMICAL REACTION; HYDROAMINATION; KNOEVENAGEL CONDENSATION; MICROWAVE RADIATION; MOLECULAR PROBE; NONHUMAN; ONE POT SYNTHESIS; POLYMERIZATION; PRIORITY JOURNAL; QUANTUM YIELD; REACTION TIME; STEREOSELECTIVITY;

EID: 84970021622     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2015.12.063     Document Type: Article

References (44)

1. 1(a) Acevedo-Rocha, C.G., Hoesl, M.G., Nehring, S., Royter, M., Wolschner, C., Wiltschi, B., Antranikian, G., Budisa, N., Catal. Sci. Technol. 3 (2013), 1198–1201.
2. 1(b) Spicer, C.D., Davis, B.G., Chem. Commun., 2011, 1698–1700.
3. 1(c) Peters, F.B., Brock, A., Wang, J., Schultz, P.G., Chem. Biol. 16 (2009), 148–152.
4. 2 Soloshonok, V.A., Izawa, K., (eds.) Asymmetric Synthesis and Application of α-amino Acids, 2009, American Chemical Society, Washington, DC.
5. 3(a) Gröger, H., Dietz, F.R., Encyclopedia of Chemical Biology, 2008, John Wiley & Sons, Weinheim, 1–12.
6. 3(b) Bommarius, A.S., Schwarm, M., Karlheinz, D., Chimia 55 (2001), 50–59.
7. 4(a) Turner, N.J., Curr. Opin. Chem. Biol. 15 (2011), 234–240.
8. 4(b) Heberling, M.W., Wu, B., Bartsch, S., Janssen, D.B., Curr. Opin. Chem. Biol. 17 (2013), 250–260.
9. 5(a) Williams, J.S., Thomas, M., Clarke, D., J. Microbiol. 151 (2005), 2543–2550.
10. 5(b) Xiang, L., Moore, B.S., J. Biol. Chem. 277 (2002), 32505–32509.
11. 5(c) Xiang, L., Moore, B.S., J. Bacteriol. 187 (2005), 4286–4289.
12. 6(a) Ritter, H., Schulz, G.E., Plant Cell 16 (2004), 3426–3436.
13. 6(b) Emiliani, G., Fondi, M., Fani, R., Gribaldo, S., Biol. Direct, 4, 2009, 7.
14. 7(a) Yamada, S., Nabe, K., Izuo, N., Nkamichi, K., Chibata, I., Appl. Environ. Microbiol. 42 (1981), 773–778.
15. 7(b) Paizs, C., Katona, A., Retey, J., Chem.—Eur. J. 12 (2006), 2739–2744.
16. 7(c) de Lange, B., Hyett, D.J., Maas, P.J.D., Mink, D., van Assema, F.B.J., Sereinig, M., de Vries, A.H.M., de Vries, J.G., ChemCatChem 3 (2011), 289–292 WILEY-VCH Verlag.
17. 7(d) Ahmed, S.T., Parmeggiani, F., Weise, N.J., Flitsch, S.L., Turner, N.J., ACS Catal. 5 (2015), 5410–5413.
18. 8 Knoevenagel, E., Chem. Ber. 31 (1898), 2596–2619.
19. 9 Doebner, O., Chem. Ber. 33 (1900), 2140–2142.
20. 10(a) Garcia-Junceda, E., Lavandera, I., Rother, D., Schrittwieser, J.H., J. Mol. Catal. B: Enzym. 114 (2015), 1–6.
21. 10(b) Ricca, E., Brucher, B., Schrittwieser, J.H., Adv. Synth. Catal. 353 (2011), 2239–2262.
22. 10(c) Santacoloma, P.A., Sin, G., Gernaey, K.V., Woodley, J.M., Org. Process Res. Dev. 15 (2011), 203–212.
23. 11(a) Paisz, C., Katona, A., Retey, J., Eur. J. Org. Chem., 2006, 1113–1116.
24. 11(b) Parmeggiani, F., Lovelock, S.L., Weise, N.J., Ahmed, S.T., Angew. Chem., Int. Ed. 54 (2015), 4608–4611.
25. 12(a) Gröger, H., Hummel, W., Curr. Opin. Chem. Biol. 19 (2014), 171–179.
26. 12(b) Gröger, H., Hummel, W., Riva, S., Fessner, W.-D., (eds.) Cascade Biocatalysis: Integrating Stereoselective and Environmentally Friendly Reactions, 2014, Wiley-VCH, Weinheim, 427–456 Chapter 19.
27. 13 Takac, S., Akay, B., Ozdamar, T.H., Enzyme Microb. Technol. 17 (1995), 445–452.
28. 14(a) Moffitt, M.C., Louie, G.V., Bowman, M.E., Pence, J., Noel, J.P., Moore, B.S., Biochemistry 46 (2007), 1004–1012.
29. 14(b) Wang, L., Gamez, A., Archer, H., Abola, E.E., Saekissian, C.N., Fitzpatrick, P., Wendt, D., Zhang, Y., Vellard, M., Bliesath, J., Bell, S.M., Lemontt, J.F., Scriver, C.R., Stevens, R.C., J. Mol. Biol. 380 (2008), 623–635.
30. 15 Kingsbury, C.A., Max, G., J. Org. Chem. 43 (1978), 3131–3139.
31. 16(a) Castro, G.R., Knubovets, T., Crit. Rev. Biotechnol. 23 (2003), 195–231.
32. 16(b) Kvittingen, L., Tetrahedron 50 (1994), 8253–8274.
33. 17 Head, D.L., McCarty, C.G., Tetrahedron Lett. 16 (1973), 1405–1408.
34. 18(a) Rodionow, W.M., Postovskaja, E.A., J. Am. Chem. Soc. 51 (1929), 841–847.
35. 18(b) Rodionow, W.M., J. Am. Chem. Soc. 51 (1929), 847–852.
36. 18(c) Tan, C.Y.K., Weaver, D.F., Tetrahedron 58 (2002), 7449–7461.
37. 19 Weise, N.J., Parmeggiani, F., Ahmed, S.T., Turner, N.J., J. Am. Chem. Soc. 137 (2015), 12977–12983.
38. 20 Lovelock, S.L., Turner, N.J., Bioorg. Med. Chem. 22 (2014), 5555–5557.
39. 21 Gloge, A., Zon, J., Kovari, A., Poppe, L., Retey, J., Chem.—Eur. J. 6 (2000), 3386–3390.
40. 22 Fujita, T., Nose, T., Matsushima, A., Okada, K., Asai, D., Yamauchi, Y., Shirasu, N., Honda, T., Shigehiro, D., Shimohigashi, Y., Tetrahedron Lett. 41 (2000), 923–927.
41. 23 Geistlinger, T.R., Guy, R.K., J. Am. Chem. Soc. 125 (2003), 6852–6853.
42. 24 Augelli-Szaffan, C.E., Horwell, D.C., Kneen, C., Ortwine, D.F., Pritchard, M.C., Purchase, T.S., Roth, B.D., Trivedi, B.K., Hill, D., Suman-Chauhan, N., Webdale, L., Bioorg. Med. Chem. 4 (1996), 1733–1745.
43. 25 Ruesbam, F.; Dragovich, P. U.S. Patent 0227774 A1. 2008.
44. 26 Studier, F.W., Prot. Expr. Purif. 41 (2005), 207–234.