Microbial/enzymatic synthesis of chiral intermediates for pharmaceuticals

Abstract There has been an increasing awareness of the enormous potential of microorganisms and enzymes for the transformation of synthetic chemicals with high chemo-, regio- and enatioselective manner. Chiral intermediates and fine chemicals are in high demand both from pharmaceutical and agrochemical industries for the preparation bulk drug substances and agricultural products. In this review article, microbial/enzymatic processes have been described for the synthesis of chiral intermediates for anticancer drugs, antiviral agents, β3-receptor agonists, antihypertensive drugs, melatonin receptor agonists, anticholesterol drugs, and anti-Alzheimer’s drugs.

[1]  M. Chartrain,et al.  Biocatalysis for pharmaceuticals--status and prospects for a key technology. , 2000, Metabolic engineering.

[2]  N. Trippodo,et al.  Dual metalloprotease inhibitors: mercaptoacetyl-based fused heterocyclic dipeptide mimetics as inhibitors of angiotensin-converting enzyme and neutral endopeptidase. , 1997, Journal of medicinal chemistry.

[3]  Ramesh N. Patel,et al.  Stereoselective enzymatic esterification of 3-benzoylthio-2-methylpropanoic acid , 1991, Applied Microbiology and Biotechnology.

[4]  T. Takeuchi,et al.  Synthesis and antitumor activity of spergualin analogues. II. Chemical modification of the spermidine moiety. , 1987, The Journal of antibiotics.

[5]  Ramesh N. Patel,et al.  Transformation of Nε-CBZ-l-lysine to CBZ-l-oxylysine using l-amino acid oxidase from Providencia alcalifaciens and l-2-hydroxy-isocaproate dehydrogenase from Lactobacillus confusus , 1992, Applied Microbiology and Biotechnology.

[6]  T. Takeuchi,et al.  Synthesis and antitumor activity of spergualin analogues. III. Novel method for synthesis of optically active 15-deoxyspergualin and 15-deoxy-11-O-methylspergualin. , 1987, The Journal of antibiotics.

[7]  J. Stewart Dehydrogenases and transaminases in asymmetric synthesis. , 2001, Current opinion in chemical biology.

[8]  L. Szarka,et al.  Stereospecific microbial reduction of 4,5-dihydro-4-(4-methoxyphenyl)-6-(trifluoromethyl-1H-1)-benzazepin+ ++-2-o ne. , 1991, Enzyme and microbial technology.

[9]  Christian Wandrey,et al.  Continuous enzymatic transformation in an enzyme membrane reactor with simultaneous NAD(H) regeneration , 1981, Biotechnology and bioengineering.

[10]  T. Takeuchi,et al.  Structure of an antitumor antibiotic, spergualin. , 1981, The Journal of antibiotics.

[11]  Ramesh N. Patel,et al.  Stereoselective reduction of β-keto esters by Geotrichum candidum , 1992 .

[12]  T. Hamilton,et al.  Synthesis and antihypertensive activity of 6,7-disubstituted trans-4-amino-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-3-ols. , 1983, Journal of medicinal chemistry.

[13]  C. Sih,et al.  Enantioselective Reductions of β‐keto‐Esters by Bakers' Yeast , 1984 .

[14]  J. Swerdel,et al.  Antihypertensive Activity During Inhibition of Neutral Endopeptidase and Angiotensin Converting Enzyme , 1991, Journal of cardiovascular pharmacology.

[15]  Ramesh N. Patel,et al.  Stereoselective biotransformations in synthesis of some pharmaceutical intermediates. , 1997, Advances in applied microbiology.

[16]  Ramesh N. Patel,et al.  Stereoselective enzymatic hydrolysis of 2-cyclohexyl-and 2-phenyl-1,3-propanediol diacetate in biphasic systems , 1990, Applied Microbiology and Biotechnology.

[17]  M. Chartrain,et al.  Bioconversion of indene to cis (1S,2R) indandiol and trans (1R,2R) indandiol by Rhodococcus species , 1998 .

[18]  Ramesh N. Patel,et al.  Stereoselective acetylation of [1-(hydroxy)-4-(3-phenyl)butyl]phosphonic acid, diethyl ester , 1997 .

[19]  Harris,et al.  Synthesis of allysine ethylene acetal using phenylalanine dehydrogenase from Thermoactinomyces intermedius. , 2000, Enzyme and microbial technology.

[20]  M. Ondetti,et al.  Inhibitors of angiotensin-converting enzyme for treatment of hypertension. , 1980, Biochemical pharmacology.

[21]  Ramesh N. Patel,et al.  Stereoselective microbial/enzymatic oxidation of (exo, exo)-7-oxabicyclo [2.2.1] heptane-2,3-dimethanol to the corresponding chiral lactol and lactone , 1992 .

[22]  J. R. Schaeffer,et al.  Preparation of L(+) β‐hydroxyisobutyric acid by bacterial oxidation of isobutyric acid , 1971, Biotechnology and bioengineering.

[23]  Ramesh N. Patel,et al.  Preparation of chiral synthon for HIV protease inhibitor: stereoselective microbial reduction of N-protected α-aminochloroketone , 1997 .

[24]  E. Frohlich,et al.  Immediate and prolonged hemodynamic effects of TA-3090 on spontaneously hypertensive [SHR] and normal Wistar-Kyoto [WKY] rats , 1988, Cardiovascular Drugs and Therapy.

[25]  M. Ondetti,et al.  Inhibition of the renin-angiotensin system. A new approach to the therapy of hypertension. , 1981, Journal of medicinal chemistry.

[26]  R. Patel,et al.  Tour de paclitaxel: biocatalysis for semisynthesis. , 1998, Annual review of microbiology.

[27]  U. Kragl,et al.  Continuous Processes with Soluble Enzymes , 1992 .

[28]  Ramesh N. Patel,et al.  Enantioselective enzymatic acetylation of racemic [4-[4α,6β (E)]]-6-[4,4-bis(4-fluorophenyl)-3-(1-methyl-1H-tetrazol-5-yl)-1,3-butadienyl]-tetrahydro-4-hydroxy-2H-pyran-2-one , 1992, Applied Microbiology and Biotechnology.

[29]  O. Ward,et al.  Reductive biotransformations of organic compounds by cells or enzymes of yeast. , 1990, Enzyme and microbial technology.

[30]  R. N. Brogden,et al.  Diltiazem. A review of its pharmacological properties and therapeutic efficacy. , 1985, Drugs.

[31]  B Rubin,et al.  Design of specific inhibitors of angiotensin-converting enzyme: new class of orally active antihypertensive agents. , 1977, Science.

[32]  R. Hanson,et al.  Site-specific enzymatic hydrolysis of taxanes at C-10 and C-13. , 1994, The Journal of biological chemistry.

[33]  Ramesh N. Patel,et al.  Microbial/enzymatic synthesis of chiral drug intermediates. , 2000, Advances in applied microbiology.

[34]  Ramesh N. Patel,et al.  Stereospecific enzymatic hydrolysis of racemic epoxide: a process for making chiral epoxide , 1999 .

[35]  C. Mcnamee,et al.  Stereoselective epoxidation of 2,2-dimethyl-2H-1-benzopyran-6-carbonitrile. , 1994, Bioorganic & medicinal chemistry.

[36]  A. Medici,et al.  Kinetic resolution of racemic secondary alcohols via oxidation with Yarrowia lipolytica strains , 2000 .

[37]  G. Edwards,et al.  Structure-activity relationships of K+ channel openers. , 1990, Trends in pharmacological sciences.

[38]  Mahmoud Mahmoudian,et al.  Biocatalytic Production of Chiral Pharmaceutical Intermediates , 2000 .

[39]  Ramesh N. Patel,et al.  NAD-linked formate dehydrogenase from methanol-grown Pichia pastoris NRRL-Y-7556. , 1982, Archives of biochemistry and biophysics.

[40]  C. Sih,et al.  Bifunctional chiral synthons via biochemical methods. 5. Preparation of (S)-ethyl hydrogen-3-hydroxyglutarate, key intermediate to (R)-4-amino-3-hydroxybutyric acid and L-carnitine. , 1984 .

[41]  R. Parker,et al.  Synthesis, biological profile, and quantitative structure-activity relationship of a series of novel 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitors. , 1990, Journal of medicinal chemistry.

[42]  D W Cushman,et al.  (Phosphinyloxy)acyl amino acid inhibitors of angiotensin converting enzyme (ACE). 1. Discovery of (S)-1-[6-amino-2-[[hydroxy(4-phenylbutyl)phosphinyl]oxy]-1-oxohexyl]-L -proline a novel orally active inhibitor of ACE. , 1988, Journal of medicinal chemistry.

[43]  Michael L. Shuler,et al.  Taxol®: science and applications. , 1995 .

[44]  Ramesh N. Patel,et al.  Asymmetric acyloin condensation catalyzed by phenylpyruvate decarboxylase , 1999 .

[45]  Ramesh N. Patel,et al.  Stereoselective enzymatic hydrolysis of (exo,exo)-7-oxabicyclo[2.2.1]heptane-2,3-dimethanol diacetate ester in a biphasic system , 1992, Applied Microbiology and Biotechnology.

[46]  Ramesh N. Patel,et al.  Deracemization of racemic 1,2-diol by biocatalytic stereoinversion , 1999 .

[47]  Wolfgang Kroutil,et al.  Asymmetric microbial hydrolysis of epoxides , 1995 .

[48]  Li Ws,et al.  Enzymic preparation of (3R‐cis)‐3‐(acetyloxy)‐4‐phenyl‐2‐azetidinone: a taxol side‐chain synthon , 1994, Biotechnology and applied biochemistry.

[49]  Ramesh N. Patel,et al.  Stereoselective acetylation of racemic 7-[N,N′-bis-(benzyloxycarbonyl)-N-(guanidinoheptanoyl)]-α-hydroxyglycine , 1997 .

[50]  C. Kawai,et al.  Comparative Effects of Three Calcium Antagonists, Diltiazem, Verapamil and Nifedipine, on the Sinoatrial and Atrioventricular Nodes: Experimental and Clinical Studies , 1981, Circulation.

[51]  M. Dawson,et al.  A practical enzymatic procedure for the resolution of N-substituted 2-azabicyclo[2.2.1]hept-5-en-3-one , 1999 .

[52]  Ramesh N. Patel,et al.  Stereoselective Microbial Reduction of 2‐Keto‐3‐(N‐Benzoylamino)‐3‐Phenyl Propionic Acid Ethyl Ester , 1995, Annals of the New York Academy of Sciences.

[53]  Ramesh N. Patel,et al.  Enzymatic synthesis of L-6-hydroxynorleucine. , 1999, Bioorganic & medicinal chemistry.

[54]  R. Furstoss,et al.  Biocatalytic Approaches for the Synthesis of Enantiopure Epoxides , 1999 .

[55]  R. Coates,et al.  Synthesis and characterization of aza analog inhibitors of squalene and geranylgeranyl diphosphate synthases. , 1992 .

[56]  M. Dutia,et al.  Disodium (R,R)-5-[2-[[2-(3-chlorophenyl)-2-hydroxyethyl]-amino] propyl]-1,3-benzodioxole-2,2-dicarboxylate (CL 316,243). A potent beta-adrenergic agonist virtually specific for beta 3 receptors. A promising antidiabetic and antiobesity agent. , 1992, Journal of medicinal chemistry.

[57]  P. Siegert,et al.  Benzoylformate decarboxylase from Pseudomonas putida as stable catalyst for the synthesis of chiral 2-hydroxy ketones. , 2000, Chemistry.

[58]  K. Faber,et al.  Biocatalytic Deracemization Techniques: Dynamic Resolutions and Stereoinversions , 1997 .

[59]  Ramesh N. Patel,et al.  Enzymatic resolution of racemic secondary alcohols by lipase B from Candida antarctica , 2000 .

[60]  R. Jain,et al.  Enzymatic kinetic resolution of piperidine atropisomers: synthesis of a key intermediate of the farnesyl protein transferase inhibitor, SCH66336. , 2000, The Journal of organic chemistry.

[61]  Ramesh N. Patel,et al.  Asymmetric acyloin condensation catalysed by phenylpyruvate decarboxylase. Part 2: Substrate specificity and purification of the enzyme , 2001 .

[62]  K. Mori,et al.  Biochemical preparations of both the enantiomers of methyl 3-hydroxypentanoate and their conversion to the enantiomers of 4-hexanolide, the pheromone of trogoderma glabrum , 1985 .

[63]  J. Martín,et al.  Chemical synthesis of allysine ethylene acetal and conversion in situ into 1-piperideine-6-carboxylic acid: key intermediate of the alpha-aminoadipic acid for beta-lactam antibiotics biosynthesis. , 1995, Bioorganic & medicinal chemistry.

[64]  T. LaPorte,et al.  Fermentation and isolation of C10-deacetylase for the production of 10-deacetylbaccatin III from baccatin III. , 1995, Biotechnology and bioengineering.

[65]  R. Hanson,et al.  Regioselective enzymatic aminoacylation of lobucavir to give an intermediate for lobucavir prodrug. , 2000, Bioorganic & medicinal chemistry.

[66]  Ramesh N. Patel,et al.  Biocatalytic preparation of a chiral synthon for a vasopeptidase inhibitor: enzymatic conversion of N2-[N-Phenylmethoxy)carbonyl] L-homocysteinyl]- L-lysine (1- > 1′)-disulfide to [4S-(4I,7I,10aJ)] 1-octahydro-5-oxo-4-[phenylmethoxy)carbonyl]amino]-7H-pyrido-[2,1-b] [1,3]thiazepine-7-carboxylic acid , 2000 .

[67]  Mary F. Malley,et al.  Synthesis of benzazepinone and 3-methylbenzothiazepinone analogs of diltiazem , 1990 .

[68]  M. Mahmoudian,et al.  Enzymic acylation of 506U78 (2‐amino‐9‐β‐D‐arabinofuranosyl‐6‐methoxy‐9H‐purine), a powerful new anti‐leukaemic agent , 1999, Biotechnology and applied biochemistry.

[69]  A. Ford-hutchinson Innovations in drug research: inhibitors of thromboxane and leukotrienes , 1991, Clinical and experimental allergy : journal of the British Society for Allergy and Clinical Immunology.

[70]  P. Siegert,et al.  Application of α-keto acid decarboxylases in biotransformations , 1998 .

[71]  Ramesh N. Patel,et al.  Microbial synthesis of chiral intermediates for β-3-receptor agonists , 1998 .

[72]  J. Barrish,et al.  Aminodiol HIV protease inhibitors. 1. Design, synthesis, and preliminary SAR. , 1994, Journal of medicinal chemistry.

[73]  Ramesh N. Patel,et al.  Enantioselective microbial reduction of 3,5-dioxo-6-(benzyloxy) hexanoic acid, ethyl ester , 1993 .

[74]  V. Gotor Pharmaceuticals Through Enzymatic Transesterification and Enzymatic Aminolysis Reactions , 2000 .

[75]  Ramesh N. Patel,et al.  Stereoselective acetylation of 3,4-dihydro-3,4-dihydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile , 1995 .

[76]  T. Hamilton,et al.  Cromakalim, nicorandil and pinacidil: novel drugs which open potassium channels in smooth muscle. , 1989, General pharmacology.

[77]  D K Robinson,et al.  Metabolic engineering and directed evolution for the production of pharmaceuticals. , 2000, Current opinion in biotechnology.

[78]  H. Sahm,et al.  Purification and properties of formaldehyde dehydrogenase and formate dehydrogenase from Candida boidinii. , 1976, European journal of biochemistry.