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Crystal structure of methyl (2R,3S)-3-[(tert-butyl-sulfin-yl)amino]-2-fluoro-3-phenyl-propano-ate.

ABSTRACT: The title compound, C14H20FNO3S, contains two chiral carbon centres and the absolute configuration has been confirmed as (2R,3S). In the crystal, adjacent mol-ecules are linked by weak C-H?O hydrogen bonds, generating zigzag chains along the a-axis direction.

SUBMITTER: Zhao Z

PROVIDER: S-EPMC4719976 | BioStudies | 2015-01-01T00:00:00Z

REPOSITORIES: biostudies

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Different intra- and inter-molecular hydrogen-bonding patterns in (3S,4aS,8aS)-2-[(2R,3S)-3-(2,5-X2-benzamido)-2-(2,5-X2-benzo-yloxy)-4-phenyl-butyl]-N-tert-butyldeca-hydro-iso-quinoline-3-carboxamides (X = H or Cl): compounds with moderate aspartyl protease inhibition activity.

Project description:The crystal structures of (3S,4aS,8aS)-2-[(2R,3S)-3-benzamido-2-benzo-yloxy-4-phenyl-but-yl]-N-tert-butyldeca-hydro-iso-quinoline-3-carboxamide, C38H47N3O4, (I), and (3S,4aS,8aS)-2-[(2R,3S)-3-(2,5-di-chloro-benzamido)-2-(2,5-di-chloro-benzo-yloxy)-4-phenyl-but-yl]-N-tert-butyldeca-hydro-iso-quinoline-3-carboxamide, C38H43Cl4N3O4, (II), are described. Despite their chemical similarity, they adopt different conformations in the solid state: (I) features a bifurcated intra-molecular N-H?(N,O) hydrogen bond from the tert-butylamide NH group to the piperidine N atom and the benzoate O atom, whereas (II) has an intra-molecular N-H?O link from the benzamide NH group to the tert-butyl-amide O atom. In the crystal of (I), mol-ecules are linked by C(4) amide N-H?O hydrogen bonds into chains propagating in the [010] direction, with both donor and acceptor parts of the benzamide group. In the extended structure of (II), C(11) N-H?O chains propagating in the [010] direction arise, with the donor being the tert-butylamide NH group and the acceptor being the O atom of the benzamide group.

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Synthesis of enantiomerically pure (2S,3S)-5,5,5-trifluoroisoleucine and (2R,3S)-5,5,5-trifluoro-allo-isoleucine.

Project description:A practical route for the stereoselective synthesis of (2S,3S)-5,5,5-trifluoroisoleucine (L-5-F3Ile) and (2R,3S)-5,5,5-trifluoro-allo-isoleucine (D-5-F3-allo-Ile) was developed. The hydrophobicity of L-5-F3Ile was examined and it was incorporated into a model peptide via solid phase peptide synthesis to determine its ?-helix propensity. The ?-helix propensity of 5-F3Ile is significantly lower than Ile, but surprisingly high when compared with 4'-F3Ile.

2013-01-01 | S-EPMC3817528 | BioStudies

Design, Synthesis, and Antiplasmodial Activity of Hybrid Compounds Based on (2R,3S)-N-Benzoyl-3-phenylisoserine.

Project description:A series of hybrid compounds based on (2R,3S)-N-benzoyl-3-phenylisoserine, artemisinin, and quinoline moieties was synthesized and tested for in vitro antiplasmodial activity against erythrocytic stages of K1 and W2 strains of Plasmodium falciparum. Two hybrid compounds incorporating (2R,3S)-N-benzoyl-3-phenylisoserine and artemisinin scaffolds were 3- to 4-fold more active than dihydroartemisinin, with nanomolar IC50 values against Plasmodium falciparum K1 strain.

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Enantioselective synthesis of (2R, 3S)- and (2S, 3R)-4,4,4-trifluoro-N-Fmoc-O-tert-butyl-threonine and their racemization-free incorporation into oligopeptides via solid-phase synthesis.

Project description:An efficient method for the enantioselective synthesis of (2R, 3S)- and (2S, 3R)-4,4,4-trifluoro-N-Fmoc-O-tert-butyl-threonine on multigram scales was developed. Absolute configurations of the two stereoisomers were ascertained by X-ray crystallography. Racemization-free coupling conditions for the incorporation of tfT into oligopeptides were then explored. For solution-phase synthesis, tfT racemization was not an issue under conventional coupling conditions. For solid-phase synthesis, the following conditions were identified to achieve racemization-free synthesis: if tfT (3.0 equiv) was not the first amino acid to be linked to the resin (1.0 equiv), the condition is 2.7 equiv DIC/3.0 equiv HOBt as the coupling reagent at 0 degrees C for 20 h; if tfT (3.0 equiv) was the first amino acid to be linked to the resin (1.0 equiv), then 1.0 equiv of CuCl(2) needs to be added to the coupling reagent.

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Bioresolution production of (2R,3S)-ethyl-3-phenylglycidate for chemoenzymatic synthesis of the taxol C-13 side chain by Galactomyces geotrichum ZJUTZQ200, a new epoxide-hydrolase-producing strain.

Project description:A newly isolated Galactomyces geotrichum ZJUTZQ200 strain containing an epoxide hydrolase was used to resolve racemic ethyl 3-phenylglycidate (rac-EPG) for producing (2R,3S)-ethyl-3-phenylglycidate ((2R,3S)-EPG). G. geotrichum ZJUTZQ200 was verified to be able to afford high enantioselectivity in whole cell catalyzed synthesis of this chiral phenylglycidate synthon. After the optimization of the enzymatic production and bioresolution conditions, (2R,3S)-EPG was afforded with high enantioselectivity (e.e.S > 99%, E > 49) after a 8 h reaction. The co-solvents, pH buffer solutions and substrate/cell ratio were found to have significant influences on the bioresolution properties of G. geotrichum ZJUTZQ200. Based on the bioresolution product (2R,3S)-EPG, taxol's side chain ethyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropionate was successfully synthesized by a chemoenzymatic route with high enantioselectivity (e.e.S > 95%).

2014-01-01 | S-EPMC6270955 | BioStudies

(2R,3S,4R)-3,4-Isopropyl-idenedi-oxy-2-(phenyl-sulfonyl-meth-yl)pyrrolidin-1-ol.

Project description:The title compound, C(14)H(19)NO(5)S, was prepared by nucleophilic addition of the lithium derivative of methyl-phenyl-sulfone to (3S,4R)-3,4-isopropyl-idene-dioxy-pyrroline 1-oxide. There are four mol-ecules in the asymmetric unit. The crystal structure determination confirms the configuration of the chiral centres as 2R,3S,4R. In the crystal, pairs of O-H?N hydrogen bonds link the mol-ecules into dimers.

2012-01-01 | S-EPMC3415002 | BioStudies

(2R,6S)-tert-Butyl 2-(benzhydryl-carbamo-yl)-6-methyl-morpholine-4-carboxyl-ate.

Project description:The title compound, C(24)H(30)N(2)O(4), was obtained by the reaction of (2R,6S)-4-(tert-but-oxy-carbon-yl)-6-methyl-morpho-line-2-carb-oxy-lic acid with diphenyl-methanamine in dimethyl-formamide solution. The morpholine ring is in a chair conformation. In the crystal, weak inter-molecular C-H?O hydrogen bonds link mol-ecules into chains along the b axis.

1000-01-01 | S-EPMC3120296 | BioStudies

(2R,3S)-2-Benzyl-3-(2,3,4,6-tetra-O-acetyl-?-d-glucopyranos-yloxy)butanolide.

Project description:The title compound, C(25)H(30)O(12), which demonstrates a significant hepatoprotective effect, has comparable geometrical parameters to those of similar compounds. The absolute configuration of the title compound, viz. 2R,3S, was identified from the Flack parameter of 0.05?(17) and the Hooft parameter of 0.04?(6).

1000-01-01 | S-EPMC2983542 | BioStudies

(1R*,2R*,3S*,4R*)-Diethyl 4-hy-droxy-4-methyl-2-(4-methyl-phen-yl)-6-oxo-cyclo-hexane-1,3-di-carboxyl-ate.

Project description:The title compound, C20H26O6, is chiral and crystallizes as a racemate: the relative configuration of the stereogenic centres is 1R*,2R*,3S*,4R*. The cyclo-hexane ring has a chair conformation. The ethyl fragment of the eth-oxy-carbonyl group in the 3-position is disordered over two sets of sites in a 0.650?(6):0.350?(6) ratio. The hy-droxy group acts as a bifurcated hydrogen-bond donor, forming both intra- and inter-molecular hydrogen bonds with ester carbonyl O atoms. The inter-molecular hydrogen bonds form inversion dimers in the crystal.

1000-01-01 | S-EPMC3648266 | BioStudies

Dichloridobis[(1S,1S',2R,2R')-(+)-1,1'-di-tert-butyl-2,2'-diphospho-lane-?P,P']ruthenium(II).

Project description:In the title compound, [RuCl(2)(C(16)H(32)P(2))(2)], the Ru(II) ion is situated on a twofold rotation axis, so the asymmetric unit contains one half-mol-ecule. The slightly distorted octa-hedral environment of the Ru center is formed by four P atoms [Ru-P = 2.4417?(6) and 2.4544?(6)?Å] from two different (1S,1S',2R,2R')-TangPhos ligands [(1S,1S',2R,2R')-TangPhos = (1S,1S',2R,2R')-(+)-1,1'-di-tert-butyl-2,2'-diphospho-lane] and two Cl atoms [Ru-Cl = 2.4267?(5)?Å].

2008-01-01 | S-EPMC2961537 | BioStudies

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