Asymmetric syntheses of (R)- and (S)-2-aminobutanesulfonic acid and their 3,3-dimethylderivatives

Braghiroli, Daniela; Bella, M. Di

doi:10.1016/0957-4166(96)00257-1

Cited by 24 publications

(8 citation statements)

References 7 publications

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“…In this study, GITC was used for precolumn derivatization of several drugs in their stereoselective study [7][8][9][10][11][12] . R-and S-TJ0711 were successfully derivatized with GITC and separated by RP-HPLC with UV detection.…”

Section: Discussionmentioning

confidence: 99%

Stereoselective HPLC assay of TJ0711 enantiomers by precolumn derivatization with GITC using UV detection and its application in pharmacokinetics in rats

Sun

Fan

et al. 2009

J. Huazhong Univ. Sci. Technol. [Med. Sci.]

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This investigation describes a new precise, sensitive and accurate stereoselective RP-HPLC method for determination of the enantiomers of a novel alpha- and beta-receptor blocking agent, 1-[4-(2-methoxyethyl) phenoxy]-3-[[2-(2- methoxyphenoxy) ethyl]amino]-2-propanol (TJ0711), in rat plasma. GITC was used for precolumn derivatization of TJ0711 enantiomers. Enantiomeric resolution was achieved on a Eurospher-100 C18 column (250 mm x 4.6 mm ID, 5-mum particle size), with UV detection at 255 nm, and the mobile phase consisted of acetonitrile and water (58:42, v/v) containing 0.02% glacial acetic acid (v/v). Using the chromatographic conditions described, TJ0711 enantiomers were well resolved with mean retention time of 10.2 and 11.5 min, respectively. Linear response (r>0.999) was observed over the range of 0.125-12.5 microg/mL of TJ0711 hydrochloride enantiomers. The mean relative standard deviation (RSD%) of the results of within-day precision was < or = 10%. The proposed method was found to be suitable and accurate for the quantitative determination of TJ0711 enantiomers in rat plasma, and it can be used in pharmacokinetic studies.

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Section: Discussionmentioning

confidence: 99%

Stereoselective HPLC assay of TJ0711 enantiomers by precolumn derivatization with GITC using UV detection and its application in pharmacokinetics in rats

Sun

Fan

et al. 2009

J. Huazhong Univ. Sci. Technol. [Med. Sci.]

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“…For background to chiral 2-amino-2-(alkyl/aryl/aralkyl)ethyl methanesulfonate hydrochlorides, see: Braghiroli & Di Bella (1996); Higashiura et al (1989); Morgan et al (1991); Pollack et al (1989); Xu (2002 Symmetry codes: (i) Àx; y À 1 2 ; Àz þ 2; (ii) Àx þ 1; y À 1 2 ; Àz þ 1; (iii) x À 1; y; z; (iv) Àx þ 1; y À 1 2 ; Àz þ 2; (v) x þ 1; y; z; (vi) Àx þ 1; y þ 1 2 ; Àz þ 2.…”

Section: Related Literaturementioning

confidence: 99%

“…The chiral 2-(alkyl/aryl/aralkyl)ethanesulfonic acid derivatives and sulfonopeptides (Higashiura et al, 1989) occur in high concentrations in many mammalian tissues. These compounds are involved in various important physiological processes and are used as enzyme inhibitors and heptans in the development of catalytic anti-bodies (Braghiroli & Di Bella, 1996). The enantiomers of chiral 2-(alkyl/aryl/aralkyl)ethanesulfonic acid derivatives mimic the hypotensive effect of taurine (2-aminoethanesulfonic acid), one of the most abundant amino acids in mammals that seems to exhibit a special affinity for excitable tissues, such as brain, nerve and muscle (Xu et al, 2002;Pollack et al, 1989;Morgan et al, 1991).…”

Section: S1 Chemical Contextmentioning

confidence: 99%

Crystal structure of (2R)-1-[(methylsulfonyl)oxy]propan-2-aminium chloride: a chiral molecular salt

Rajegowda¹,

Palakshamurthy²,

Lokanath³

et al. 2015

Acta Cryst E

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In the title chiral molecular salt, C4H12NO3S+·Cl−, the cation is protonated at the N atom, producing [RNH3]+, where R is CH3SO2OCH2C(H)CH3. The N atom in the cation is sp 3-hybridized. In the crystal, cations and anions are connected by strong N—H⋯Cl hydrogen bonds to generate edge-shared 12-membered rings of the form {⋯Cl⋯HNH}3. This pattern of hydrogen bonding gives rise to zigzag supramolecular layers in the ab plane. The layers are connected into a three-dimensional architecture by C—H⋯O hydrogen bonds. The structure was refined as an inversion twin.

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“…Rac-N-Boc-tert-leucine methylester (6) was synthesized according to the procedure of Braghiroli and Di Bella. 43 Rac-N-Boc-tert-leucine benzylester (7) was synthesized as described previously. 44 …”

Section: Synthesismentioning

confidence: 99%

Preparative resolution of the enantiomers of Tert‐leucine derivatives by simulated moving bed chromatography

et al. 2002

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The enantiomers of two different derivatives of tert-leucine were separated by continuous chromatography on chiral stationary phases applying the simulated moving bed technique. About 1 kg of racemic N-carbobenzoxy-tert-leucine was resolved on the cellulose-based phase Chiralcel OD using a mixture of heptane/ethanol and 0.1% of trifluoroacetic acid modifier as the mobile phase, while 520 g of the N-Boc-tert-leucine-benzylester was resolved on the amylose-based phase Chiralpak AD with a mixture of heptane/2-propanol as the mobile phase. In both instances the corresponding enantiomers were obtained in high yield and high optical purity.

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Asymmetric syntheses of (R)- and (S)-2-aminobutanesulfonic acid and their 3,3-dimethylderivatives

Cited by 24 publications

References 7 publications

Stereoselective HPLC assay of TJ0711 enantiomers by precolumn derivatization with GITC using UV detection and its application in pharmacokinetics in rats

Stereoselective HPLC assay of TJ0711 enantiomers by precolumn derivatization with GITC using UV detection and its application in pharmacokinetics in rats

Crystal structure of (2R)-1-[(methylsulfonyl)oxy]propan-2-aminium chloride: a chiral molecular salt

Preparative resolution of the enantiomers of Tert‐leucine derivatives by simulated moving bed chromatography

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