Biocatalysis for Green Chemistry and Drug Development

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1 PROGRESS IN CHEMISTRY Vol. 19 No. 12 Dec., ,3 3 3 (1., ; 2., ; 3. BioVerdant, Inc., 7330 Carroll Road, San Diego, CA 92121, USA), ( GenBank) (PDB),, :,, : Q814 ; O : A : X(2007) Biocatalysis for Green Chemistry and Drug Development Chen Zhenming 1 Liu Jinhua 2 Tao, Junhua 2,3 3 3 (1. College of Biological & Environmental Engineering, Zhejiang University of Technology, Hangzhou , China ; 2. College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou , China ; 3. BioVerdant, Inc., 7330 Carroll Road, San Diego, CA 92121, USA) Abstract Biocatalysis is becoming a transformational technology for chemical synthesis as a result of recent breakthroughs in biotechnology exponential growth in publically available sequences from the gene database and protein data bank ( PDB), efficient molecular cloning and protein expression platforms, powerful directed enzyme evolution technologies to improve biocatalyst s specificity, selectivity and stability. In this review, the focus will be directed to its applications in drug manufacturing to deliver cost2effective chemoenzymatic processes, green chemistry to minimize the generation of wastes and usage of hazardous reagents, and natural product modification to discover novel therapeutics with improved biological profiles. Key words synthesis ; metabolic engineering GenBank ; protein data bank ( PDB ) ; biocatalysis ; green chemistry ; natural products ; drug,, 1 (, ), [1 ] [4,5 ], [2,3 ],ruprintrivir [6,, ] : (No ) (No. R406378) 3 3 e2mail :junhua - com

2 , ketomethylene peptidomimetic, P 1, P 2, P 3 P 4 4, [15,16 ( 1) ] P 2 (80 % 88 %) ee ( > 9919 %) P 2 [7,8 ] 5, [7,8 ] 1 P 2 ruprintrivir Scheme 1 Synthesis of ruprintrivir from P 2 [7,8 ] ( GSSM TM ), 190 [18 ],,, 3molΠL,, ( substrate modulation) 16 h 100 %, ee 99 % [19 ] (medium engineering), [9 11 ], pelitrexol GARFT, 20, 2 %, Sonogashira, 9, 10 % 15 % [12 ] 2 pregabalin [7,8 ] [7,8 ] Scheme 2 Synthesis of pregabalin by nitrilases ( R)242 cyano232hydroxybutyric acid ( ) ( 3) 24 h 32 (HGN) ( R) , 3molΠL ee 88 % [17 ] (process engineering) 3 [17 19 ], Scheme 3 Synthesis of atorvastatin by directed evolution of [17 nitrilases 19 ],, ( ) (statin) HMG2CoA ( pregabalin (Lyrica TM ) Lipitor TM Crestor TM ) ( 4), ( 2), 52 (DERA) 2 1, Arabidopsis (20 % wtπwt) thaliana, [7,8 ] ( ( 2 gπl) R), DERA, 2 % (wtπwt),,

3 gπlπh [20,21 ] 4 DERA 6),, [20,21 ] Scheme 4 Synthesis of statin drugs by DERA2catalyzed aldol [20,21 ] reaction,, ( S)2 5,, [22 ] (throughput) 2 5 pregabalin [25 ] Scheme 5 Chemical synthesis of pregabalin by classic resolution [25 ] [26 28 ],, 6 3, 12, [23,24 ] [26 28 ] 6 Pregabalin, Scheme 6 A green chemoenzymatic process for the synthesis [26 of pregabalin 28 ],,,,,,,,,, 2, 2 62 ( stoichiometric amount) (62APA) (72 Lyrica TM pregabalin ADCA) 62APA 72ADCA ( 5),cyanodiester (CNDE) , 2, G [25 ] (9915 %), G (API), ( S)2,, ( 25 % 29 % 7,62APA, R = H OH) [29 ], 18 %,, N, N2 21 %, 70 % ( ;, - 40 ) (, G

4 [29 ] Scheme 9 Synthesis of oseltamivir phosphate from shikimic 7 2 [31,32 ] Scheme 7 Chemical synthesis of semi2synthetic acid 2lactam antibiotics [29 ] [33,34, ] [35 ], G, 62APA 84 gπl, 2, 33 % [33 ] Tamiflu R,,, (, 8) [30 ] 72ADCA Tamiflu R API [30 ] 8 2, Scheme 8 Enzymatic synthesis of semi2synthetic 2lactam, Bacillus pumilus ATCC antibiotics [30 ] mediterranei aminodahp,,kanosamine,, 5 % [37 ] ;, 22 %,, (oseltamivir phosphate, Tamiflu R ) ( 9), Tamiflu R, Roche 10 [31,32 ],, 3 [31,32 ] 9 [36 39 ],, ( 10) [40 ] kanosamine ; Amycolatopsis API 10 [40 ],, Scheme 10 A new ( 9) aminoshikimic acid, route to oseltamivir phosphate via

5 , [44, ] (Taxol R ), ( Taxus brevifolia), % [41,42 ],,,,, 102 ( Scheme [43 11) 45 ] 102 ( Taxus baccata), Scheme 12 Biosynthesis of paclitaxel from pyrophosphates 011 %,, 45 ] , Scheme 11 Synthesis of paclitaxel from 102deacetyl baccatin 10 [43 [43 48 ] 12 [52,53,, 11 ] 7,,, (NRP), (PK) [54 ] CoA [55 ] [56 ] [46 ( 12) 48 ], ( 13),, taxa24 (5), 11 (12)2diene,, [57 ], 311 [49 51 ], [58 ], ( Taxus media) mgπl, [59, ], [46 (pregabalin),, 3

6 ] 13 [54 Scheme 13 Biosynthesis of NRP PK and terpenoids 56 ] S N 2 [54 ( ), ( 15) [64 ],, [65,66 ],, [60,61 ], 72 FADH2 [62 ] 72,, (, 14) [63 ] L2 2 [64 ] 15 Scheme 15 Biosynthesis of coronatine via enzymatic chlorination [64 ], 42 [67 ] S2, L2 52 ( 16) [63 ] 18 F 14 [68 ] Scheme 14 Synthesis of rebeccamycin analogs by halogenases [63 ] 312, NRP PK (coronatine) (post2synthase),,

7 [67 ] Scheme 16 Biosynthesis of 42fluorothreonine by fluorinase [67 ] 18, A (tyrocidine A), N Scheme 18 Synthesis of glycosylated non2ribosomal peptides [71 ] C S N 2, by enzymatic macrocyclization [71 ] [69 ], ( TI) 6, 18 42,,, NRP, 4 PK, fengycin, Π synthase C O ( PPΠPK, 17) [70 ] [72 ] ; PK, [73 75 ] 313, 17 PPΠPKs [70 ] Scheme 17 Enzymatic synthesis of novel macrocyclic PPΠPKs by cyclases [70 ],, Lin [71 ] 247 A ( Tyc A) (AA =, 18), 1,32 19, Tyc A [77,78 ], Scheme 19 Synthesis of novel glycopeptides by enzymatic Tyc4PG214 Tyc A glycosylation and acylation [77,78 ]

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