Preparation of Optically Active 2-Thiazolidinecarboxylic Acid by Asymmetric Transformation.

Shiraiwa, Tadashi; Katayama, Takashi; Ishikawa, Joji; Asai, Takeshi; Kurokawa, Hidemoto

doi:10.1248/cpb.47.1180

Cited by 10 publications

(9 citation statements)

References 1 publication

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“…3, the racemization rate constants k of the 2‐THC isomers were calculated (Table 1). The rate constants are in good agreement with literature values 11…”

Section: Resultsmentioning

confidence: 99%

“…The compounds used were a salt of (+)‐2‐THC with (2 S , 3 S )‐tartaric acid ((+)‐2‐THC·( S )‐TA), and a salt of (−)‐2‐THC with (2 R , 3 R )‐tartaric acid (−)‐2‐THC·( R )‐TA). The compounds were synthesized by a published method 11. In addition, L ‐ and D ‐proline were used as comparison to the 2‐THC isomers.…”

Section: Methodsmentioning

confidence: 99%

“…Shiraiwa et al prepared optically active 2‐THC via asymmetric transformation by taking advantage of its rapid racemization in solution. They determined the absolute configuration of (+)‐2‐THC to have a (S)‐configuration and (−)‐2‐THC to have an (R)‐configuration in reference to the molecular rotation of the following five compounds: (2 R , 4 R )‐ and (2 S , 4 R )‐2,4‐thiazolidine dicarboxylic acid, ( R )‐4‐thiazolidinecarboxylic acid, and (+)‐ and (−)‐2‐THC 11. It is anticipated that the intensity of the associated complexes between 2‐THC and [Sb 2 ( L ‐tart) 2 ] 2− or [Sb 2 ( D ‐tart) 2 ] 2− will change as 2‐THC undergoes racemization.…”

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confidence: 99%

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Zinc(II) Coordination Complexes as Membrane‐Active Fluorescent Probes and Antibiotics

DiVittorio¹,

Leevy²,

O’Neil³

et al. 2008

ChemBioChem

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Molecular probes with zinc(II)-(2,2'-dipicolylamine) coordination complexes associate with oxyanions in aqueous solution and target biomembranes that contain anionic phospholipids. This study examines a new series of coordination complexes with 2,6-bis(zinc(II)-dipicolylamine) phenoxide as the molecular recognition unit. Two lipophilic analogues are observed to partition into the membranes of zwitterionic and anionic vesicles and induce the transport of phospholipids and hydrophilic anions (carboxyfluorescein). These lipophilic zinc complexes are moderately toxic to mammalian cells. A more hydrophilic analogue does not exhibit mammalian cell toxicity (LD 50 >50 µg/mL), but it is highly active against the Gram-positive bacteria Staphylococcus aureus (MIC of 1 µg/mL). Furthermore, it is active against clinically important S. aureus strains that are resistant to various antibiotics including vancomycin and oxacillin. The antibiotic action is attributed to its ability to depolarize the bacterial cell membrane. The intense bacterial staining exhibited by a fluorescent conjugate suggests that this family of zinc coordination complexes can be used as molecular probes for the detection and imaging of bacteria.

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“…3, the racemization rate constants k of the 2‐THC isomers were calculated (Table 1). The rate constants are in good agreement with literature values 11…”

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 99%

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Zinc(II) Coordination Complexes as Membrane‐Active Fluorescent Probes and Antibiotics

DiVittorio¹,

Leevy²,

O’Neil³

et al. 2008

ChemBioChem

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“…Therefore, the resolution of this racemic thiazolidine-2-carboxylic acid is an important problem in the determination of its enantiomeric purity. Shiraiwa et al [10] ever used tartaric acid as the resolving agent for resolution of racemic thiazolidine-2-carboxylic acid. Thus, it is very important to determine the enantiomeric purity of thiazolidine-2-carboxylic acid in pharmaceutical preparations.…”

Section: Introductionmentioning

confidence: 99%

HPLC determination of enantiomeric thiazolidine-2-carboxylic acid on chiral stationary phase with pre-column derivatization

Zhang

Peng

Zeng

et al. 2013

Acta Chromatographica

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Summary.A new high-performance liquid chromatography (HPLC) method has been developed and validated for determination of enantiomeric purity of thiazolidine-2-carboxylic acid within a short run time of less than 10 min. The method was based on pre-column derivatization of thiazolidine-2-carboxylic acid with aniline, and complete separation of enantiomers has been achieved on a Chiralcel OD-H analytical column (250 × 4.6 mm) using n-hexane-isopropanol (85:15 v/v) as mobile phase at a flow rate of 1.0 mL min −1 under UV and optical rotation (OR) detection. Detection wavelength was set at 254 nm. Then the effects of mobile phase and temperature on enantioselectivity were further evaluated. The method was validated with respect to precision, accuracy, linearity, limit of detection (LOD), limit of quantification (LOQ), and robustness. The recoveries were between 98.5 and 101.3% with percentage relative standard deviation less than 1.16%. The LOD and LOQ for the aniline derivatives of (+)-thiazolidine-2-carboxylic acid were 4.9 and 16.4 μg mL −1 and for the aniline derivatives (−)-thiazolidine-2-carboxylic acid were 5.1 and 17.2 μg mL −1 , respectively.

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“…Johnson et al 1 reported the resolution of racemate of thiazolidine-2-carboxylic acid ester in ethanol and ether medium but yield is ranging between 43 -47%. Shiraiwa et al 8 synthesized optically active thiazolidine carboxylic acid by asymmetric transformation in acetic acid and ethanol medium using (+) or (-) tartaric acid salt and further hydrolysis of salt in triethylamine and methanol gave only ~50% optically active thiazolidine carboxylic acid. This prompted us to develop an efficient crystallization induced dynamic resolution for thiazolidine-2-carboxylic acid derivative.…”

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confidence: 99%

Crystallization Induced Dynamic Resolution of Ethyl Thiazolidine-2-Carboxylate

Kang¹,

Park²,

Thopate³

et al. 2010

Bulletin of the Korean Chemical Society

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Preparation of Optically Active 2-Thiazolidinecarboxylic Acid by Asymmetric Transformation.

Cited by 10 publications

References 1 publication

Zinc(II) Coordination Complexes as Membrane‐Active Fluorescent Probes and Antibiotics

Zinc(II) Coordination Complexes as Membrane‐Active Fluorescent Probes and Antibiotics

HPLC determination of enantiomeric thiazolidine-2-carboxylic acid on chiral stationary phase with pre-column derivatization

Crystallization Induced Dynamic Resolution of Ethyl Thiazolidine-2-Carboxylate

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