Lipase-catalyzed synthesis of ethyl (R)-2-benzyloxy-2-isopropylhydrogenmalonate: a useful combination of chemical synthesis with enzymatic methods

References

• Sinz A. Die Bedeutung der Mutterkorn‐Alkaloide als Arzneistoffe. Weit mehr als nur α‐Blocker. Pharm Unserer Zeit. 2008;37:306–309.
   PubMedGoogle Scholar
• Somei M, Yokoyama Y, Murakami Y, et al. Recent synthetic studies on the Ergot alkaloids and related compounds. J Cheminform. 2001;32:191–257.
   Google Scholar
• Flieger M, Wurst M, Shelby R. Ergot alkaloids-sources, structures and analytical methods. Folia Microbiol. 1997;42:3–30.
   PubMed Web of Science ®Google Scholar
• Lee MR. The history of ergot of rye (Claviceps purpurea) III: 1940-80. JR Coll Physicians Edinburgh. 2010;40:77–80.
   PubMedGoogle Scholar
• Parkes JD, Marsden CD, Donaldson I, et al. Bromocriptine treatment in Parkinson’s disease. J Neurol Neurosurg Psychiatry. 1976;39:184–193.
   PubMed Web of Science ®Google Scholar
• Eadie MJ. Ergot of rye-the first specific for migraine. J Clin Neurosci. 2004;11:4–7.
   PubMed Web of Science ®Google Scholar
• Schiff PL Jr. Ergot and its alkaloids. Am J Pharm Educ. 2006;70:98.
   PubMed Web of Science ®Google Scholar
• Cheng JZ. Nature’s approach toward ring formation and structural diversity in ergot alkaloid biosynthesis. Doctoral dissertation, Massachusetts Institute of Technology, (2011).
   Google Scholar
• Stadler PA, Guttmann S, Hauth H, et al. Die Synthese der Alkaloide der Ergotoxin-Gruppe. 70. Mitteilung über Mutterkornalkaloide [1]. Helv Chim Acta. 1969;52:1549–1564.
   PubMedGoogle Scholar
• Moldvai I, Temesvári-Major E, Incze M, et al. Enantioefficient synthesis of α-ergocryptine: first direct synthesis of (+)-lysergic acid. J Org Chem. 2004;69:5993–6000.
   PubMed Web of Science ®Google Scholar
• Pogorevc M, Faber K. Biocatalytic resolution of stereically hindered alcohols, carboxylic acids and esters containing fully substituted chiral centers by hydrolytic enzymes. J Mol Catal B. 2000;10:357–376.
   Google Scholar
• Sugai T, Higashibayashi S, Hanaya K. Recent examples of the use of biocatalysts with high accessibility and availability in natural product synthesis. Tetrahedron. 2018;74:3469–3487.
   Web of Science ®Google Scholar
• Hansen TV, Waagen V, Partali V, et al. Co-solvent enhancement of enantioselectivity in lipase-catalysed hydrolysis of racemic esters. A process for production of homochiral C-3 building blocks using lipase B from Candida antarctica. Tetrahedron: Asymmetry. 1995;6:499–504.
   Google Scholar
• Kato K, Gong Y, Saito T, et al. Efficient preparation of optically active ketoprofen by Mucor javanicus lipase immobilized on an inorganic support. J Biosci Bioeng. 2000;90:332–334.
   PubMed Web of Science ®Google Scholar
• Zhang LQ, Zhang YD, Xu L, et al. Lipase-catalyzed synthesis of RGD diamide in aqueous water-miscible organic solvents. Enzyme Microb Tech. 2001;29:129–135.
   Web of Science ®Google Scholar
• Chen Y, Xu JH, Pan J, et al. Catalytic resolution of (RS)-HMPC acetate by immobilized cells of Acinetobacter sp. CGMCC 0789 in a medium with organic cosolvent. J Mol Catal B. 2004;30:203–208.
   Google Scholar
• Fernández-Lorente G, Palomo JM, Mateo C, et al. Fernandez-Lafuente, R. Resolution of paroxetine precursor using different lipases: influence of the reaction conditions on the enantioselectivity of lipases. Enzyme Microb Tech. 2004;34:264–269.
   Web of Science ®Google Scholar
• Zhang W, Ni Y, Sun Z, et al. Biocatalytic synthesis of ethyl (R)-2-hydroxy-4-phenylbutyrate with Candida krusei SW2026: a practical process for high enantiopurity and product titer. Process Biochem. 2009;44:1270–1275.
   Web of Science ®Google Scholar
• Bansode SR, Hardikar MA, Rathod VK. Evaluation of reaction parameters and kinetic modelling for Novozym 435 catalysed synthesis of isoamyl butyrate. J Chem Technol Biotechnol. 2017;92:1306–1314.
   Web of Science ®Google Scholar
• Villalba M, Verdasco-Martín CM, Dos Santos JC, et al. Operational stabilities of different chemical derivatives of Novozym 435 in an alcoholysis reaction. Enzyme Microb Tech. 2016;90:35–44.
   PubMed Web of Science ®Google Scholar
• Polloni AE, Chiaradia V, Figura EM, et al. Polyesters from macrolactones using commercial lipase NS 88011 and Novozym 435 as Biocatalysts. Appl Biochem Biotech. 2018;184:659–672.
   PubMed Web of Science ®Google Scholar
• Karlsson S. Development of an Enantioselective Novozym 435 mediated acetylation for the preparation of (1 S, 3 R)-3-Acetamidocyclohexane-1-carboxylic acid. Org Process Res Dev. 2016;20:1336–1340.
   Web of Science ®Google Scholar
• Dong HP, Wang YJ, Zheng YG. Enantioselective hydrolysis of diethyl 3-hydroxyglutarate to ethyl (S)-3-hydroxyglutarate by immobilized Candida antarctica lipase B. J Mol Catal B. 2010;66:90–94.
   Google Scholar
• Long WS, Kow PC, Kamaruddin AH, et al. Comparison of kinetic resolution between two racemic ibuprofen esters in an enzymic membrane reactor. Process Biochem. 2005;40:2417–2425.
   Web of Science ®Google Scholar
• Basheer S, Mogi K, Nakajima M. Surfactant‐modified lipase for the catalysis of the interesterification of triglycerides and fatty acids. Biotechnol Bioeng. 1995;45:187–195.
   PubMed Web of Science ®Google Scholar
• Zaks A, Klibanov A,M. Enzymatic catalysis in nonaqueous solvents. J Biol Chem. 1988;263:3194–3201.
   PubMed Web of Science ®Google Scholar