Page 334 - Cascade_Biocatalysis_Integrating_Stereoselective_and_Environmentally_Friendly_Reactions
P. 334
310 14 Enzymatic Stereoselective Synthesis of -Amino Acids
8. Gerfaud, T., Chiang, Y.-L., Kreituss, β-amino acids: synthesis and activity
I., Russak, J.A., and Bode, J.W. (2012) against Candida albicans. Bioorg. Med.
Enantioselective, chromatography-free Chem. Lett., 13, 433–436.
3
synthesis of β -amino acids with natural 18. Wolin, R.L., Santill´ an, A. Jr.,, Barclay,
and unnatural side chains. Org. Process T., Tang, L., Venkatesan, H., Wilson, S.,
Res. Dev., 16, 687–696. Lee, D.H., and Lovenberg, T.W. (2004)
9. Kamal, A. and Ramesh Khanna, G.B. Novel glycine transporter type-2 reup-
(2001) A facile preparation of (±)-β- take inhibitors. Part 2: β-and γ-amino
hydroxy nitriles and their enzymatic acid derivatives. Bioorg. Med. Chem., 12,
resolution with lipases. Tetrahedron: 4493–4509.
Asymmetry, 12, 405–410.
19. Zhu, Y., Wu, G., Zhu, X., Ma, Y., Zhao,
10. Kamal, A., Ramesh Khanna, G.B., and X., Li, Y., Yuan, Y., Yang, J., Yu, S.,
Ramu, R. (2002) Chemoenzymatic
Shao, F., and Lei, M. (2010) Synthesis,
synthesis of both enantiomers of flu-
in vitro and in vivo biological evaluation,
oxetine, tomoxetine and nisoxetine:
and comprehensive understanding of
lipase-catalyzed resolution of 3-aryl-3-
structure-activity relationships of dipep-
hydroxypropanenitriles. Tetrahedron:
tidyl boronic acid proteasome inhibitors
Asymmetry, 13, 2039–2051.
constructed from β-amino Acids. J. Med.
11. Kinfe, H.H., Chhiba, V., Frederick, J.,
Bode, M.L., Mathiba, K., Steenkamp, Chem., 53, 8619–8626.
P.A., and Brady, D. (2009) Enan- 20. Armour, D.R., Bell, A.S., Edwards, P.J.,
tioselective hydrolysis of β-hydroxy Ellis, D., Hepworth, D., Lewis, M.L.,
nitriles using the whole cell biocatalyst and Smith, C.R. (2004) Preparation of
Rhodococcus rhodochrous ATCC BAA-870. heterocyclylcarboxamides as oxytocin
J. Mol. Catal. B: Enzym., 59, 231–236. inhibitors. PCT Patent WO2004/020414.
12. Chhiba, V.P., Bode, M.L., Mathiba, K., 21. Angelaud, R., Armstrong, J.D., Askin,
Kwezi, W., and Brady, D. (2012) Enan- D., Balsells, J., Hansen, K., Lee, J.,
tioselective biocatalytic hydrolysis of Maligres, P.E., Rivera, N.R., Xiao, Y.,
β-aminonitriles to β-amino-amides using and Zhong, Y.L. (2004) Process for
Rhodococcus rhodochrous ATCC BAA-870. the preparation of β-amino acid amide
J. Mol. Catal. B: Enzym., 76, 68–74. dipeptidyl peptidase-IV inhibitors. PCT
13. Fix, J.A. (1996) Oral controlled release Patent WO2004/087650.
technology for peptides: status and 22. Imbriglio, J., Colletti, S.L., Tata, J.R.,
future prospects. Pharm. Res., 13, Beresis, R.T., Marley, D., Raghavan, S.,
1760–1764.
Schmidt, D.R., Lins, A.R., Smenton,
14. Olson, G.L., Bolin, D.R., Bonner, M.P.,
A.L., Chen, W., Shen, H., Ding, F.-
B¨ os, M., Cook, C.M., Fry, D.C., Graves,
X., and Bodner, R. (2006) Preparation
B.J., Hatada, M., Hill, D.E., Khan,
of (hetero) aryl amino acid amides as
M., Madison, V.S., Rusiecki, V.K., niacin receptor agonists for treatment of
Sarabu, R., Sepinwall, J., Vincent, G.P., atherosclerosis, dyslipidemia, diabetes,
and Voss, M.E. (1993) Concepts and
and metabolic syndrome. PCT Patent
progress in the development of peptide
mimetics. J. Med. Chem., 36, 3039–3049. WO2007/075749.
15. Godballe, T., Nilsson, L.L., Petersen, 23. Aguilar, M.-I., Purcell, A.W., Devi,
R., Lew, R., Rossjohn, J., Smith, A.I.,
P.D., and Jenssen, H. (2011) Antimicro-
bial β-peptides and α-peptoids. Chem. and Perlmutter, P. (2007) β-Amino
Biol. Drug Des., 77, 107–116. acid-containing hybrid peptides -new
16. Vagner, J., Qu, H., and Hruby, V.J. opportunities in peptidomimetics. Org.
(2008) Peptidomimetics, a synthetic tool Biomol. Chem., 5, 2884–2890.
of drug discovery. Curr. Opin. Chem. 24. Weiner, B., Szyma´ nski, W., Janssen,
Biol., 12, 292–296. D.B., Minnaard, A.J., and Feringa, B.L.
17. Mittendorf, J., Kunisch, F., Matzke, (2010) Recent advances in the catalytic
M., Militzer, H.-C., Schmidt, A., and asymmetric synthesis of beta-amino
Sch¨ onfeld, W. (2003) Novel antifungal acids. Chem.Soc.Rev., 39, 1656–1691.