Optical resolution of 1-(1-naphthyl)ethylamine by its dicarboxylic acid derivatives: Structural features of the oxalic acid derivative diastereomeric salt pair

Optical resolution methods were established for racemic 1-(1-naphthyl) ethylamine. The resolving agents were synthesized by N-derivatizing (R)-1-(1-naphthyl) ethylamine with dicarboxylic acids. Oxalic, malonic, and succinic acid derivatives were found to be suitable resolving agents. These resolutions are parallel to a series of optical resolutions of 1-phenylethylamine which had been previously performed by our research group using similar derivative resolving agents (Balint et al., Tetrahedron: Asymmetry 2001;12:1511-1518.) The comparison of the results of the enantiomer separations is performed. The diastereomeric salts formed with (R)-N-[1-(1-naphthyl)ethyl]oxalamic acid were investigated by single crystal X-ray diffraction. The crystal structures were compared with the previously published structures of the diastereomers of the phenyl-substituted analogue, namely (R)- and (S)-1-phenylethylammonium (R)-N-(1-phenylethyl)oxalamates (Balint et al., Tetrahedron: Asymmetry 2001;12:1511-1518).     

Stereospecific HPLC method for the quantitation of the enantiomers of MK-0571, a potent leukotriene D4 receptor antagonist, in biological specimens.

A stereospecific HPLC bioanalytical method was developed for quantitation of the enantiomers of MK-0571, a leukotriene D4 receptor antagonist. The procedure involves the addition of an internal standard analog to the biological matrix followed by extraction of the free acids into ethyl acetate. The acids are subsequently reacted with the homochiral reagent, (+)-(R)-alpha-(1-naphthyl)ethylamine (NEA) to form diastereomers. Following removal of excess reagent and side products by a dilute acid wash, the NEA-MK-0571 diastereomers are separated on a phenyl urea chiral column using a mobile phase containing hexane, isopropanol, and acetonitrile and are detected with a fluorescence detector. The sensitivity of the method is such that 50 ng of each enantiomer can be quantitated. In the 0.05 to 10 micrograms range the recoveries of the enantiomers of MK-0571 from plasma were 100.4 +/- 7.9% and 100.0 +/- 7.2%. NMR and mass spectral data confirmed the structure of the derivative. The method has been utilized in drug safety evaluation studies to demonstrate enantioselectivity in disposition of the enantiomers of MK-0571 in rats and monkeys but not in mice.     

普萘洛尔对映异构体诱导HUVEC细胞的蛋白质表达谱差异

手性药物只能通过严格的手性识别才能选择性地与特定生物大分子相互作用,在药动学、药效学等方面上表现出手性特征.以非选择性β肾上腺素能受体阻滞剂普萘洛尔（PRO）的对映异构体R(+)/S(-)-PRO为模型药物,分别作用于人脐静脉内皮细胞（HUVEC）,提取全细胞蛋白质,经双向电泳、MALDI-TOF-MS、SWISSPROT数据库分析鉴定差异表达蛋白质;共筛选出22个差异表达蛋白质点,鉴定了HSP86、HSP84、GRP75、KLC18、KBTB2、TGM2、GBLP、GCNT2、RAB36、KLH34等10种蛋白质.研究表明,PRO对映异构体可引起广泛的基因表达改变,涉及信号分子、代谢酶、骨架蛋白、伴侣蛋白等,且具有显著的手性特征,这可能与PRO显著的手性生物学特征有紧密联系,但仍需开展进一步深入研究,以明确产生PRO手性生物学特征的多种途径和机制.蛋白质组学技术为深入了解药物的手性生物学特征及其作用机制提供了新的思路和策略,对手性药物开发和临床合理用药有着重要的意义.     

Chiral separation of pheniramine-like 3-phenyl-3-heteroarylpropylamines by CE and HPLC methods

Analytical CE and HPLC methods were developed for the chiral separation of halogen-substituted 3-phenyl-3-(2-pyridyl)propylamines 1-4 (1: 3-(4-fluorophenyl) approximately, 2: 3-(3,4-difluorophenyl) approximately, 3: 3-(4-chlorophenyl) approximately, 4: 3-(3,4-dichlorophenyl) approximately ), 3-(4-fluorophenyl)-3-(2-thiazolyl)propylamine (5), and 3-(4-fluorophenyl)-3-(1-benzylimidazol-2-yl)propylamine (6), which are building blocks for the preparation of very potent arpromidine-type histamine H(2) receptor agonists. All amines were enantioseparated by CE with resolutions of at least 1.8 using alpha-, beta-, or gamma-cyclodextrin (CD) as chiral selectors. With heparin as buffer additive for CE the optical antipodes of 1-4 and 6 were separated with resolutions > or = 1.8. On RP-18 columns the separation of the (+)-(S)-acetylmandelic acid amides of racemic 2 (R = 0.9, alpha = 1.07) and the thioureas prepared by addition of 6 to 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl isothiocyanate (R = 2.0, alpha = 1.20) was successful, whereas the diastereomeric ureas prepared from 3 and (+)-(S)-1-(1-naphthyl)ethyl isocyanate could not be resolved. Separation of the diastereomeric isoindoles prepared from 1-5, o-phthaldialdehyde and 2,3,4,6-tetra-O-acetyl-1-thio-beta-D-glucopyranoside was achieved on a RP-18 phase (R > or = 0.4, a > or = 1.02). Direct separation of the enantiomers of 3 and 4 was achieved on a Cyclobond I column (R > or = 0.9, alpha > or = 1.07). alpha- and beta-CD were also useful as mobile phase additives for HPLC (3 and 4: RP-18 column, beta-CD, R > or = 0.4, alpha > or = 1.03; 3: RP-18 column, alpha-CD: R = 0.5, alpha = 1.04).     

Chiral enamines derived from 2-(2′-pyrido)acetophenone and 2-(2′-quinolino)acetophenone as ligands in copper(I) catalyzed enantioselective cyclopropanations

Optically active enamines of 2-(2′-pyrido)acetophenone or 2-(2′-quinolino)acetophenone with (R)-1-phenylethylamine, (R)-1-(1-naphthyl)ethylamine, (R)-cyclohexylethylamine, and (R)-phenylglycinol were prepared and their copper(I) complexes used in the enantioselective cyclopropanation of styrene with ethyl- and menthyldiazoacetate. Enantioselectivities of up to 42% enantiomeric excess were obtained for cis/trans 2-phenylcyclopropan-1-carboxylic acid ethyl esters, as determined by gas-liquid chromatography (GLC) on chiral chromatographic columns. © 1995 Wiley-Liss, Inc.     

Broad sensitivity of rodent arrhythmia models to class I, II, III, and IV antiarrhythmic agents

To determine specificity of rodent models of arrhythmia for different Vaughan Williams classes of antiarrhythmic drugs, we tested 17 drugs from the four classes in one in vitro and four in vivo models. In the mouse chloroform-induced ventricular fibrillation model and in the guinea pig ouabain-induced arrhythmia model, drugs of classes I (amefalone, aprindine, lidocaine, mexiletine, phenytoin, procainamide, or quinidine), II (metoprolol or propranolol), and IV (bepridil) were active. Class III drugs (bretylium, clofilium, or melperone did not suppress ouabain arrhythmias, but were active in the mouse chloroform model. In the rat coronary artery ligation model, disopyramide (class I), amefalone and melperone significantly (P less than 0.05) reduced the number of extrasystoles. Propranolol, sotalol, and verapamil (class IV) were less effective. In the rat coronary artery ligation/reperfusion model, all four classes of antiarrhythmic agents were active in vitro (isolated heart) and in vivo (anesthetized rat). Thus, one model of automaticity, the guinea pig ouabain model, detected class I, II, and IV drugs, whereas another automaticity model, the mouse chloroform model, also detected class III agents. The model of reentry induced by ischemia plus reperfusion (rat coronary artery ligation reperfusion) can be recommended as a screen for new antiarrhythmic agents based on its sensitivity to all four classes of antiarrhythmic drugs. The Vaughan Williams class of an antiarrhythmic agent must be determined, however, by additional mechanism studies.     

Chiral discrimination of multiple profens as diastereomeric (R)-(+)-1-phenylethylamides by achiral dual-column gas chromatography

Profens were converted into diastereomeric (R)-(+)-1-phenylethylamides using ethyl chloroformate and triethylamine in dichloromethane. Gas chromatographic analysis on dual-columns with different polarities provided complete enantioresolution of eight profens, facilitating chiral discrimination based on matching with retention index sets characteristic of each enantiomer. The present method was linear (r >/= 0.9992) with good precision (0.8-6.0%) and accuracy (-9.3 to 0.003%), allowing detection of trace (R)-profens in optical purity test on four (S)-profen mixture in a single run. And the method allowed simultaneous enantiomeric screening for ibuprofen enantiomers and their chiral metabolites excreted in urine following administration of racemic ibuprofen.     

Effect of sialic acid residues of human α1-acid glycoprotein on stereoselectivity in basic drug-protein binding

The function of sialic acid groups at the terminal of sugar chains of human α₁-acid glycoprotein (AGP) was investigated with respect to chiral discrimination between optical isomers of basic drugs, using high-performance capillary electrophoresis/frontal analysis (HPCE/FA), a novel analytical method developed for the determination of unbound drug concentration with ultramicrosample volume (100–200 nl). Native human AGP and desialylated AGP were used as test proteins, and propranolol (PRO) and verapamil (VER) were used as model drugs. The unbound concentration of (S)-VER was 1.31 times higher than that of (R)-VER in native AGP solution. This selectivity was not affected by desialylation. Further, enzymatic elimination of galactose residues, which neighbored sialic acid groups, did not change the binding of either isomer of VER. On the other hand, the unbound concentration of (R)-PRO was 1.27 times higher than that of (S)-PRO in native AGP solution. Desialylation caused the unbound concentration of (S)-PRO to rise to the same level of (R)-PRO, resulting in loss of enantioselectivity. Thus, it follows that sialic acid groups of AGP, as a whole, are not responsible for chiral recognition between enantiomers of VER but are involved in enantioselectivity toward the isomers of PRO. Chirality 9:291–296, 1997. © 1997 Wiley-Liss, Inc.     

Synthesis of enantiopure phthalides including 3-butylphthalide, a fragrance component of celery oil, and determination of their absolute configurations

Enantiopure phthalides 2 and 5-8 were synthesized via enantioresolution of the corresponding alcohols with a chiral auxiliary of camphorsultam dichlorophthalic acid, (1S,2R,4R)-(-)-CSDP acid 3, followed by solvolysis with KOH in MeOH and the catalytic oxidation of chiral glycols with iridium complex 28. The absolute configurations of phthalides 2 and 5-8 were determined by applying the (1)H-NMR anisotropy method of MalphaNP acid (4), 2-methoxy-2-(1-naphthyl)propionic acid, to the chiral synthetic precursory alcohols. In the case of 3-phenylphthalide (R)-(-)-7, the absolute configuration determined by the (1)H-NMR anisotropy method using MalphaNP acid 4 agreed with that by the X-ray crystallographic method. By applying these methods, 3-butylphthalide (S)-(-)-2, a fragrance component of essential oil of celery, has been synthesized in an enantiopure form, and its absolute configuration was unambiguously determined.     

Enzymatic resolution of racemic amines in a continuous reactor in organic solvents

An enzymatic process has been developed for the continuous production of the pharmaceutically important intermediate (R)-1-aminoindan and of the chiral resolving agent (R)-1-(1-naphthyl)ethylamine. The process consists of the subtilisin catalyzed stereoselective aminolysis of the racemic primary amine with an active ester in organic solvent. The competing nonenzymatic reaction has been suppressed by appropriate choice of solvent and reactant's concentration and by minimizing the time of contact between the amine and the active ester. Subtilisin was immobilized on glass beads and the reaction carried out in a continuous-flow column bioreactor. By using a 450-mL column bioreactor containing 5.7 g of subtilisin immobilized on 570 g of glass beads, 1.6 kg of racemic 1-(1-naphthyl)ethylamine was resolved after 320 h of continuous operation with only a slight loss of the enzymatic activity. During the whole process, the optical purity of the chiral amine eluting from the column was higher than 90%. A facile procedure was developed for separating the unreacted (R)-amine from the (S)-amide and for the recycling of the solvent 3-methyl-3-pentanol and the active ester 2,2,2-trifluoroethyl butyrate. (c) 1992 John Wiley & Sons, Inc.     

Circular dichroism of host-guest complexes of achiral pyridino- and phenazino-18-crown-6 ligands with the enantiomers of chiral aralkyl ammonium salts

Circular dichroism (CD) spectroscopy was used for distinguishing different types of chiral interactions in host-guest complexes of achiral pyridino- and phenazino-18-crown-6 ligands with chiral aralkyl ammonium salts. The general feature of the CD spectra of many homochiral (e.g., (R,R)-host and (R)-guest) and heterochiral (e.g., (R,R)-host and (S)-guest) alpha-(1-naphthyl)ethylamine hydrogenperchlorate salt (NEA) complexes with chiral pyridino- and phenazino-18-crown-6 hosts is exciton interaction. The most interesting example is the coupling of the transitions of the chiral guest NEA with the energetically close transitions of the achiral phenazino-18-crown-6 host 6. The CD spectrum of the complex is predominated by exciton coupling between the (1)B(b) transition of the chiral guest and the (1)B(b) transition of the achiral host. The redshifted intense spectra of the complexes of (R)- or (S)-1-phenylethylamine hydrogenperchlorate salt (PEA) with the achiral diester-pyridino-18-crown-6 host 4 are indicative of merging the pi electron systems into one joint charge transfer chromophore. The appearance of weak bands with alternating sign in the spectrum of PEA complexes of the achiral "parent" pyridino-18-crown-6 host (1) indicates the presence of two or more conformers. The CD spectra of the complexes of achiral phenazino-18-crown-6 host 6 with PEA are also determined by pi-pi interaction. In addition to charge transfer bands, CD bands are also induced in the long-wavelength spectral region of the achiral host. The weak pi-pi interaction between the achiral phenazino-18-crown-6 host and methyl phenylglycinate hydrogenperchlorate (PGMA) or methyl phenylalaninate hydrogenperchlorate (PAMA) does not result in a definite spectral effect in the (1)L(a) region of the spectrum of the chiral guest, but its existence is proven by the weak CD bands induced in the long-wavelength spectral region of the achiral host.     

1,3,5-Triazine multiselector systems: New tools for chiral discrimination

2-Hexylamino-4-[(S)-1-(1-naphthyl)ethylamino]-6-L-valyl-L-valyl-L-valine isopropylester-1,3,5-triazine (1), a molecule characterized by two different chiral selectors, and 2-hexylamino-4,6-bis-L-valyl-L-valyl-L-valine isopropylester-1,3,5-triazine (2) and 2-ethoxy-4-hexylamino-6-[(S)-1-(1-naphthyl) ethylamino]-1,3,5-triazine (3), systems in which a single kind of chiral selector is present, have been prepared. The enantiodiscriminating ability in solution of the three compounds toward the N-3,5-dinitrobenzoyl derivatives of 1-phenylethylamine (4) or valine methylester (5) has been investigated by ¹H nuclear magnetic resonance (NMR) spectroscopy: 1 shows an improved versatility, relative to 2 and 3, as a chiral solvating agent for NMR spectroscopy. On the basis of the indications obtained, the usefulness of 2-chloro-4-[(S)-1-(1-naphthyl)ethylamino]-6-L-val-L-val-L-valine isopropylester-1,3,5-triazine (1a), a direct precursor of 1, as chiral solvating agent for the determination by NMR of the enantiomeric compositions of derivatives of amines, amino alcohols, amino acids, and carboxyl acids bearing a 3,5-dinitrophenyl moiety, has been demonstrated. Chirality 9:113–121, 1997. © 1997 Wiley-Liss, Inc.     

New method for the resolution of the enantiomers of 5,6-Dihydroxy-2-Methyl-Aminotetralin by selective derivatization and HPLC analysis: Application to biological fluids

A new chiral derivatization procedure for the HPLC resolution of chiral catecholamines and structurally related compounds is described. The homochiral reagent, (+)-(R)-1-phenylethyl isocyanate (RPEIC), was added to separate and quantitate the enantiomers of rac-5,6-dihydroxy-2-methyl-aminotetralin, the main metabolite of rac-5,6-diisobutyryl-2-methyl-aminotetralin, a potent dopamine agonist, by reversed-phase HLPC analysis. To avoid catecholamine degradation in the basic reaction medium and to obtain the selective and quantitative derivatization of the amino group of the compound, the reversible complex formation between diphenylborinic acid (DPBA) and the catechol group, in alkaline medium, was performed before homochiral isocyanate addition. The RPEIC derivatization was completed in 30 min and then the DPBA complex was dissociated by adding dilute acid. The structure of intermediates and urea derivatives was confirmed by mass spectrometry. The use of an electrochemical detector, operating in redox mode, allowed HPLC quantitation of enantiomers at the nanogram level in plasma and urine. The derivatization procedure is also suitable for other catecholamine-related compounds. © 1996 Wiley-Liss, Inc.     

N2-benzyl-N1-(1-(1-naphthyl)ethyl)-3-phenylpropane-1,2-diamines and conformationally restrained indole analogues: development of calindol as a new calcimimetic acting at the calcium sensing receptor

The synthesis and calcimimetic activities of two new families of compounds are described. The most active derivatives of the first family, N(2)-(2-chloro-(or 4-fluoro-)benzyl)-N(1)-(1-(1-naphthyl)ethyl)-3-phenylpropane-1,2-diamine (4b and 4d, respectively, tested at 10 microM) produced 98+/-6% and 95+/-4%, respectively, of the maximal stimulation of [(3)H]inositol phosphates production obtained by 10mM Ca(2+) in CHO cells expressing the rat calcium sensing receptor (CaSR). The second family of calcimimetics was obtained by conformationally restraining the compounds of type 4 to provide the 2-aminomethyl derivatives 5. One of these compounds, (R)-2-[N-(1-(1-naphthyl)ethyl)aminomethyl]indole ((R)-5a, calindol), displayed improved calcimimetic activity compared to 4b and 4d as well as stereoselectivity. In the presence of 2mM Ca(2+), calindol stimulated [(3)H]inositol phosphates accumulation with an EC(50) of 1.0+/-0.1 or 0.31+/-0.05 microM in cells expressing the rat or the human CaSR, respectively. The calcimimetic activities of these novel compounds were shown to be due to a specific interaction with the CaSR.     

Determination of enantiomeric excess of ethyl 3,5-dihydroxy-6-benzyloxy hexanoate by chiral reverse phase high performance liquid chromatography

A simple and reliable chiral HPLC method was developed for the determination of enantiomeric excess of a chiral dihydroxy intermediate for the chemoenzymatic synthesis of side chain of statin drugs. After evaluating different columns and conditions, the four stereoisomers of ethyl 3,5-dihydroxy-6-benzyloxy hexanoate were well resolved by a simple gradient elution on OD-RH column, and the enantiomeric excess of the desired 3R,5S-enantiomer was accurately measured. This study provides a simple, rapid, accurate, and reliable method to assess the enantiomeric quality of such important intermediates.     

Stereospecific synthesis and absolute configuration of mexiletine

Data on the absolute configuration of mexiletine (MEX) do not appear to have been published, although in several published reports the configuration is referred to as (?)-(R) and (+)-(S), based on information from manufactures providing the drug stereoisomers. We demonstrate that (?)-MEX has the (R)-configuration by mean of a new stereospecific synthesis. X-Ray analysis of an optical active sample of (+)-MEX as its hydrobromide salt, obtained from chemical resolution of the racemic mixture, was carried out in order to obtain precise information on bond lengths and angles, useful for studies on structure–activity relationships. We also report the NMR analysis in presence of Eu(hfc)₃ as shift reagent, which represents a simple method for the determination of enantiomeric excess (ee) in addition to the well-known chiral HPLC methods. © 1994 Wiley-Liss, Inc.     

Chiral derivatization for separation of racemic amino and thiol drugs by liquid chromatography and capillary electrophoresis

Separation of racemic amino drugs (α-methylbenzeneethanamine, 6-amino-2-methyl-2-heptanol and 1-aminoethyl-benzenemethanol) and thiol drugs [N-(2-mercapto-1-oxopropyl) glycine, 2-mercaptopropanoic acid, and N-acetyl-3-mercaptovaline] has been evaluated after derivatization. ortho-Phthalaldehyde (OPA) and naphthalene-2,3-dicarboxaldehyde (NDA) were used with either homochiral thiols (N-acetyl-L-cysteine and N-acetyl-D-penicillamine) or amines [(-)-(1R,2S)-norephedrine, L-phenylalanine, L-tyrosine, and 3-hydroxy-L-tyrosine] as chiral selectors according to the analyte reactive group. The resulting 36 diastereoisomeric derivatives were studied using reversed-phase high-performance liquid chromatography (RP-HPLC) and capillary electrophoresis (CE). Of the CE modes, micellar electrokinetic chromatography (MEKC) using sodium dodecyl sulfate (SDS) as surfactant, β-cyclodextrin (β-CD)-modified capillary zone electrophoresis (β-CD-CZE), and β-CD-MEKC were applied. Results highlight respective performance of the reagents and separative techniques. All OPA derivatives of racemic amino drugs were resolved either by MEKC or β-CD-MEKC. In the case of racemic thiol drugs, 10 of the 12 OPA derivatives were resolved in β-CD-CZE. © 1995 Wiley-Liss, Inc.     

Synthesis and biological evaluation of benzopyran analogues bearing class III antiarrhythmic pharmacophores

We have synthesized a series of compounds combining the hydroxy-benzopyran ring of vitamin E with the methylsulfonylaminophenyl group of class III antiarrhythmic drugs, connected through tertiary amine moieties. Evaluation of the antiarrhythmic and antioxidant activity of the new compounds was carried out on isolated rat heart preparations using the non-recirculating Langendorff mode. The new analogues were present, at 10 microM concentration, during ischemia and reperfusion. Selected compounds were further studied by a conventional microelectrode method in order to get insight into their cellular mode of action. The most active compound, N-[4-[2-[[2-(3,4-dihydro-6-hydroxy-2,2,7,8-tetramethyl-2H-1-benzopyran-5-yl)ethyl] methylamine]ethyl]phenyl]methanesulfonamide (19a), reduces premature beats, prolongs QT and QRS intervals during ischemia and reperfusion, and reduces MDA content, leading to a fast recovery of the heart. In addition, it exhibits moderate class III antiarrhythmic action.     

Combinations of chiral and prochiral singlet radical-pairs in reaction cavities of polyethylene films. Control and analysis of radical tumbling and translation.

The regio- and stereo-chemistries of combination products from chiral 1-naphthoxy/(R)-2-phenylpropanoyl and prochiral 1-naphthoxy/1-phenylethyl singlet radical-pairs (radical-pairs A and B, respectively) have been studied at different temperatures in polyethylene (PE) films with different crystallinities. The radical-pairs have been generated as intermediates along the photo-Fries reaction course of 1-naphthyl (R)-2-phenylpropanoate ((R)-1) and the photo-Claisen reaction course of 1-naphthyl (R)-1-phenylethyl ether ((R)-2). Radical-pair was produced directly upon lysis of the first excited singlet state of (R)-2 and indirectly after irradiation of (R)-1 and subsequent decarbonylation of the 2-phenylpropanoyl radical of radical-pair A. Comparison of the fates of the directly and indirectly formed radical-pairs provides detailed information about the nature of the reaction cavities within the polyethylene hosts and how the combinations of the radical-pairs are influenced by their initial locations within a cavity. The results, especially when taken with those from irradiations in n-alkanes, indicate that the cavities are "templated" by the (R)-1 and (R)-2 guest molecules and that the templated shapes are retained in some form for periods that are at least as long as the time required for decarbonylation of a 2-phenylpropanoyl radical. In addition, the enantiomeric excesses of the decarbonylated photoproducts from (R)-1(2, 2-(1-phenylethyl)-1-naphthol (2BN), and 4-(1-phenylethyl)-1-naphthol (4BN)) or 2BN and 4 BN from (R)-2 indicate different influences of temperature on translational and tumbling motions of the radicals of radical-pairs B within their polyethylene cages.     

Chemoenzymatic synthesis of optically active, biodegradable polymers based on phenyl- and naphthyl-ethanols esterified with divinyladipate

For the purpose of developing a new synthetic polymer containing an asymmetric molecule branch, three racemic alcohols, i.e. 1-phenylethanol, 1-(4-methylphenyl)ethanol and 1-(2-naphthyl)ethanol, were esterified enzymatically with divinyladipate using a lipase from Pseudomonas cepacia. The enzymatic acylation of alcohols produced monoacylated products. Optically active polymerizable monomers, (R)-vinyl adipic acid (phenyl-1-yl) ethyl ester, (R)-vinyl adipic acid (4-methylphenyl-1-yl) ethyl ester and (R)-vinyl adipic acid (2-naphthyl-1-yl) ethyl ester with enantiometric excesses over 99%, 96% and 99%, respectively, were obtained. Each optically active monomer was then subjected to free radical polymerization, to give polymers having a number average molecular weight of 2.9 x 10(3) - 2.2 x 10(4). These polymers are considered useful as optically active polymers having biodegradability.