74
Views
0
CrossRef citations to date
0
Altmetric
Research Article

Enzymatic approach to the synthesis of chiral intermediate of Rodatristat ethyl

, , , , , & show all
Received 05 Sep 2023, Accepted 04 Nov 2023, Published online: 16 Nov 2023

Reference

  • Amrutkar SM, Banoth L, Banerjee UC. 2013. One-pot synthesis of (R)-1-(1-naphthyl) ethanol by stereoinversion using Candida parapsilosis. Tetrahedron Lett. 54(25):3274–3277. doi: 10.1016/j.tetlet.2013.04.051.
  • Banoth L, Banerjee UC. 2017. New chemical and chemo-enzymatic synthesis of (RS)-,(R)-, and (S)-esmolol. Arab J Chem. 10(2):S3603–S3613. doi: 10.1016/j.arabjc.2014.03.011.
  • Banoth L, Devarapalli K, Paul I, Thete KN, Pawar SV, Banerjee UC. 2021. Screening, isolation and selection of a potent lipase producing microorganism and its use in the kinetic resolution of drug intermediates. J Indian Chem Soc. 98(10):100143. doi: 10.1016/j.jics.2021.100143.
  • Baydaş Y, Dertli E, Şahin E. 2020. Green synthesis of chiral aromatic alcohols with Lactobacillus kefiri P2 as a novel biocatalyst. Synth Commun. 50(7):1035–1045. doi: 10.1080/00397911.2020.1729809.
  • Chin KM, Rubin LJ. 2008. Pulmonary arterial hypertension. J Am Coll Cardiol. 51(16):1527–1538. doi: 10.1016/j.jacc.2008.01.024.
  • Daniel P. 2020. Crystalline spirocyclic compound, a dosage form containing, a method for using in treatment of disease, and a method for recrystallizing. US 20200148681A1.
  • Imam HT, Marr PC, Marr AC. 2021. Enzyme entrapment, biocatalyst immobilization without covalent attachment. Green Chem. 23(14):4980–5005. doi: 10.1039/D1GC01852C.
  • Kalay E, Şahin E. 2021a. Regioselective asymmetric bioreduction of trans-4-phenylbut-3-en-2-one by whole-cell of Weissella cibaria N9 biocatalyst. Chirality. 33(9):535–542. doi: 10.1002/chir.23337.
  • Kalay E, Şahin E. 2021b. Biocatalytic asymmetric synthesis of (R)-1-tetralol using Lactobacillus paracasei BD101. Chirality. 33(8):447–453. doi: 10.1002/chir.23318.
  • Kamble AL, Banoth L, Meena VS, Singh A, Chisti Y, Banerjee UC. 2013. Nitrile hydratase of Rhodococcus erythropolis: characterization of the enzyme and the use of whole cells for biotransformation of nitriles. 3 Biotech. 3(4):319–330. doi: 10.1007/s13205-012-0104-2.
  • Kethavath SN, Patlolla RR, Rosangzuala K, Polumati A, Nemali M, Pawar SV, Banoth L. 2023. Lipase catalyzed chemo-enzymatic synthesis of propranolol: newer enzymatic approach. J Indian Chem Soc. 100(7):101037. 101037. doi: 10.1016/j.jics.2023.101037.
  • Lazarus HM, Denning J, Wring S, Palacios M, Hoffman S, Crizer K, Kamau‐Kelley W, Symonds W, Feldman J. 2022. A trial design to maximize knowledge of the effects of Rodatristat Ethyl in the treatment of pulmonary arterial hypertension (ELEVATE 2). Pulm Circ. 12(2):e12088. doi: 10.1002/pul2.12088.
  • Martin de MI, Cruz-Utrilla A, Oliver E, Escribano-Subias P. 2023. Novel molecular mechanisms involved in the medical treatment of pulmonary arterial hypertension. Int J Mol Sci. 24(4):4147. doi: 10.3390/ijms24044147.
  • Özdemir A, Şahin E. 2022. Efficient bioreduction of cyclohexyl phenyl ketone by Leuconostoc pseudomesenteroides N13 biocatalyst using a distance-based design-focused optimization model. Mol Catal. 528:112474. doi: 10.1016/j.mcat.2022.112474.
  • Pai O, Banoth L, Ghosh S, Chisti Y, Banerjee UC. 2014. Biotransformation of 3-cyanopyridine to nicotinic acid by free and immobilized cells of recombinant Escherichia coli. Process Biochem. 49(4):655–659. doi: 10.1016/j.procbio.2014.01.023.
  • Patil R, Banoth L, Singh A, Chisti Y, Banerjee UC. 2013. Enantioselective bioreduction of cyclic alkanones by whole cells of Candida Species. Biocatal Biotransfor. 31(3):123–131. doi: 10.3109/10242422.2013.778252.
  • Ravichandra K, Balaji R, Devarapalli K, Batchu UR, Thadikamala S, Banoth L, Pinnamaneni SR, Prakasham RS. 2023. Enzymatic production of prebiotic xylooligosaccharides from sorghum (Sorghum bicolor (L.) xylan: value addition to sorghum bagasse. Biomass Conv Bioref. 13(12):11131–11139. doi: 10.1007/s13399-021-02216-z.
  • Şahin E, Dertli E. 2017. Highly enantioselective production of chiral secondary alcohols with Candida zeylanoides as a new whole cell biocatalyst. Chem Biodivers. 14(9):e1700121. doi: 10.1002/cbdv.201700121.
  • Şahin E, Dertli E. 2019. Biocatalyzed enantiomerically pure production of (S)-Phenyl (thiophen-2-yl) methanol. J Heterocyclic Chem. 56(10):2884–2888. doi: 10.1002/jhet.3681.
  • Şahin E, Serencam H, Dertli E. 2019. Whole cell application of Lactobacillus paracasei BD101 to produce enantiomerically pure (S)-cyclohexyl (phenyl) methanol. Chirality. 31(3):211–218. doi: 10.1002/chir.23048.
  • Şahin E. 2017. Debaryomyces hansenii as a new biocatalyst in the asymmetric reduction of substituted acetophenones. Biocatal.Biotransfor. 35(5):363–371. doi: 10.1080/10242422.2017.1348500.
  • Şahin E. 2018. Production of (R)-1-(1, 3-benzodioxol-5-yl) ethanol in high enantiomeric purity by Lactobacillus paracasei BD 101. Chirality. 30(2):189–194. doi: 10.1002/chir.22782.
  • Şahin E. 2019. Green synthesis of enantiopure (S)-1-(benzofuran-2-yl) ethanol by whole-cell biocatalyst. Chirality. 31(10):892–897. doi: 10.1002/chir.23123.
  • Şahin E. 2020. First green synthesis of (R)-2-methyl-1-phenylpropan-1-ol using whole-cell Lactobacillus paracasei BD101 biotransformation. Biocatal Biotransfor. 38(2):138–143. doi: 10.1080/10242422.2019.1698554.
  • Şahin E. 2023. Efficient bioreduction of 1-(furan-2-yl) ethanone into enantiomerically pure drug precursor by Lactobacillus paracasei BD101. Mol Catal. 539:113037. doi: 10.1016/j.mcat.2023.113037.
  • Specker E, Matthes S, Wesolowski R, Schütz A, Grohmann M, Alenina N, Pleimes D, Mallow K, Neuenschwander M, Gogolin A, et al. 2022. Structure-based design of xanthine-benzimidazole derivatives as novel and potent tryptophan hydroxylase inhibitors. J Med Chem. 65(16):11126–11149. doi: 10.1021/acs.jmedchem.2c00598.
  • Stéphane De L, Daniel RG. 2016. Processes for preparing (R)-1-(5-chloro-1,1-biphenyl-2-yl)-2,2,2-trifluoroethanol and 1-(5-chloro-1,1-biphenyl-2-yl)-2,2, 2-trifluoroethanone. US 2016O257633A1.
  • Stéphane De L, Daniel RG, Kenneth B, Eric BS. 2015. Spirocyclic compounds as tryptophan hydroxylase inhibitors. US009 199994B2.
  • Tietze LF, Zhou Y, Töpken E. 2000. Synthesis of simple enantiopure tetrahydro‐β‐carbolines and tetrahydroisoquinolines. Eur J Org Chem. 2000(12):2247–2252. doi: 10.1002/1099-0690(200006)2000:12<2247::AID-EJOC2247>3.0.CO;2-4.
  • Tozlu N, Bülbül AS, Özdemir A, Şahin E. 2023. Efficient bio-catalytic production of enentiopure (S)-(4-chlorophenyl)(phenyl) methanol as a drug precursor by using a novel rotatable composite design-based optimization strategy. Mol Catal. 547:113404. doi: 10.1016/j.mcat.2023.113404.
  • Yadav JS, Reddy BVS, Padmavani B, Venugopal C, Rao AB. 2007. 2007. Enzymatic kinetic resolution of racemic 4-tetrahydropyranols by Candida rugosa lipase. Tetrahedron Lett. 48(26):4631–4633. doi: 10.1016/j.tetlet.2007.04.091.
  • Yılmaz D, Şahin E, Dertli E. 2017. Highly enantioselective production of chiral secondary alcohols using Lactobacillus paracasei BD 101 as a new whole cell biocatalyst and evaluation of their antimicrobial effects. Chem Biodivers. 14(11):e1700269. hdlhandlenet/20.500.12403/2217
  • Zheng W, Wang Z, Jiang X, Zhao Q, Shen J. 2020. Targeted drugs for treatment of pulmonary arterial hypertension: past, present, and future perspectives. J Med Chem. 63(24):15153–15186. doi: 10.1021/acs.jmedchem.0c01093.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.