Abstract
The resolution of 2-amino alcohols protected by urethane-type groups either via porcine pancreatic lipase (PPL) hydrolysis of the corresponding racemic acetates or via PPL catalyzed transesterification of racemic alcohols was studied. In both cases, Boc protecting group led to better chemical yields and enantiopurities than Z and Fmoc protecting groups. Furthermore, a simple and efficient method for the synthesis of the medicinally interesting optically pure (R)-2- aminohexadecanol was developed.
Keywords: 2-Amino alcohols, enzymatic hydrolysis, enzymatic resolution, porcine pancreatic lipase, transesterification
Letters in Organic Chemistry
Title: Resolution of N-Protected Amino Alcohols by Porcine Pancreatic Lipase
Volume: 7 Issue: 2
Author(s): Victoria Magrioti, Irene Fotakopoulou, Nicolaos Athinaios, Panoula Anastasopoulou, Violetta Constantinou-Kokotou and George Kokotos
Affiliation:
Keywords: 2-Amino alcohols, enzymatic hydrolysis, enzymatic resolution, porcine pancreatic lipase, transesterification
Abstract: The resolution of 2-amino alcohols protected by urethane-type groups either via porcine pancreatic lipase (PPL) hydrolysis of the corresponding racemic acetates or via PPL catalyzed transesterification of racemic alcohols was studied. In both cases, Boc protecting group led to better chemical yields and enantiopurities than Z and Fmoc protecting groups. Furthermore, a simple and efficient method for the synthesis of the medicinally interesting optically pure (R)-2- aminohexadecanol was developed.
Export Options
About this article
Cite this article as:
Magrioti Victoria, Fotakopoulou Irene, Athinaios Nicolaos, Anastasopoulou Panoula, Constantinou-Kokotou Violetta and Kokotos George, Resolution of N-Protected Amino Alcohols by Porcine Pancreatic Lipase, Letters in Organic Chemistry 2010; 7 (2) . https://dx.doi.org/10.2174/157017810790796327
DOI https://dx.doi.org/10.2174/157017810790796327 |
Print ISSN 1570-1786 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6255 |
- Author Guidelines
- Graphical Abstracts
- Fabricating and Stating False Information
- Research Misconduct
- Post Publication Discussions and Corrections
- Publishing Ethics and Rectitude
- Increase Visibility of Your Article
- Archiving Policies
- Peer Review Workflow
- Order Your Article Before Print
- Promote Your Article
- Manuscript Transfer Facility
- Editorial Policies
- Allegations from Whistleblowers
Related Articles
-
Extracts and Flavonoids of <i>Passiflora</i> Species as Promising Anti-inflammatory and Antioxidant Substances
Current Pharmaceutical Design Evolutionary Computation and QSAR Research
Current Computer-Aided Drug Design Epidemiology, Evolution, Transmission, and Therapeutics of COVID-19 Outbreak: An Update on the Status
Coronaviruses Outpatient Treatment of Hemorrhoidal Disease: The Alternative Way to Treat Hemorrhoidal Disease in a Simple, Safe and Effective Manner
Reviews on Recent Clinical Trials Bee Pollen: Chemical Composition and Potential Beneficial Effects on Health
Current Nutrition & Food Science A Novel Synthesis Method of Apogossypolone and its Antitumor Activity
Letters in Drug Design & Discovery Allosteric Modulation of Nicotinic Acetylcholine Receptors: The Concept and Therapeutic Trends
Current Pharmaceutical Design Live Impedance Measurements and Time-lapse Microscopy Observations of Cellular Adhesion, Proliferation and Migration after Ionizing Radiation
Current Pharmaceutical Biotechnology Trends in the Design and Application of Optical Chemosensors in Pharmaceutical and Biomedical Analysis
Current Pharmaceutical Analysis Multicomponent Synthesis of Novel Class of Isatin and 5-isatinyli-denerhodanine Based Diaminofuran Derivatives
Letters in Organic Chemistry Feature Based Fusion of Multimodal Medical Image Slices with Combined Transforms
Current Medical Imaging Drug Acyl Glucuronides: Reactivity and Analytical Implication
Current Pharmaceutical Analysis Diabetic Gastroenteropathy: Soothe the Symptoms or Unravel a Cure?
Current Diabetes Reviews Characterization of Pharmaceutical IgG and Biosimilars Using Miniaturized Platforms and LC-MS/MS
Current Pharmaceutical Biotechnology Double Layered Hydroxides as Potential Anti-Cancer Drug Delivery Agents
Mini-Reviews in Medicinal Chemistry Cysteine Proteinases of Trypanosome Parasites Novel Targets for Chemotherapy
Current Drug Targets The Antitumor Efficiency of Zinc Finger Nuclease Combined with Cisplatin and Trichostatin A in Cervical Cancer Cells
Anti-Cancer Agents in Medicinal Chemistry Oxidative Stress and Antioxidant Potential of One Hundred Medicinal Plants
Current Topics in Medicinal Chemistry Esterase Activities in the Blood, Liver and Intestine of Several Preclinical Species and Humans
Drug Metabolism Letters Reproductive Toxicology of Environmental Toxicants: Emerging Issues and Concerns
Current Pharmaceutical Design