Table 4 Comparison of whole-cell conversion and chemical synthesis of chiral alcohols and their pharmaceutical importance
| Â | Pharmaceutical intermediate structure | Whole-cell catalysis | Chemical synthesis | ||||
|---|---|---|---|---|---|---|---|
% Product (A)* | % Product (B)** | (S) Â %EE (A)* | (S) Â %EE (B)** | In-house Chemically synthesized compounds | Product and Pharmaceutical use | ||
1 | 3,4-Methylenedioxyphenyl acetone
| 95 | 90 | 90 | 82 | (S)-2-methyloxirane and n-Butyl Lithium [49] | Talampanel Treatment of Epilepsy. Non-competitive antagonist against glutamate receptor [50] |
2 | 1-N-carbobenzoxy-3-pyrrolidone
| 96.8 | 96 | 97 | 50 | Sodium borohydride catalyst [51] | Barnidipine Calcium Channel Blocker [52] |
3 | 1-(3,5-Bis-trifluoromethyl-phenyl)-ethanone
| 23.8 | 77 | 100 | 44 | DIP chloride used, difficult chemistry in large scale [53] | Aprepitant Treating chemotherapy induced vomiting. Blocks NK1 receptor [54] |
4 | 1- (2,6-Dichloro-3-fluoro-phenyl)-ethanone
| 40.2 | 40 | 100 | 92 | Ruthenium metal based Naud’s catalyst [55] | Crizotinib Anti-cancer drug, an anaplastic lymphoma kinase inhibitor [56] |
5 | 3-Trifluoromethyl acetophenone
| 91.1 | 91 | 100 | 91 | Asymmetric hydrogenation of keto substrate using Noyori’s ruthenium (II) catalyst [57] | MA-20565 Agricultural Broad spectrum fungicide [58] |
6 | 2-Phenyl-1-thiazol-2-yl-ethanone
| 100 | 100 | 96 | 89.3 | Asymmetric hydrogenation of keto substrate using ligated copper hydride in presence of polymethyl hydrosiloxane [59] | Dolastatin Anti-tumor agent [60] |
7 | 1- (3-methoxyphenyl) ethanone
| 97.5 | 97 | 98 | 98 | Asymmetric hydrogenation of keto substrate using ruthenium complexes [61, 62] | Rivastigmine Treatment of moderate dementia related to Parkinson’s and Alzheimer’s disease [63] |
8 | 3-Oxo-4- (2,4,5-trifluoro-phenyl)-butyric acid methyl ester
| 98.3 | 98 | 46 | 99 | Asymmetric hydrogenation is done by using Adam’s catalyst which is very expensive [48] | Sitagliptin Used for treating diabetes mellitus type 2 [64] |
