109429-01-8Relevant academic research and scientific papers
Total Synthesis of the Congested, Bisphosphorylated Morganella morganii Zwitterionic Trisaccharide Repeating Unit
Keith, D. Jamin,Townsend, Steven D.
supporting information, p. 12939 - 12945 (2019/08/22)
Zwitterionic polysaccharides (ZPSs) activate T-cell-dependent immune responses by major histocompatibility complex class II presentation. Herein, we report the first synthesis of a Morganella morganii ZPS repeating unit as an enabling tool in the synthesis of novel ZPS materials. The repeating unit incorporates a 1,2-cis-α-glycosidic bond; the problematic 1,2-trans-galactosidic bond, Gal-β-(1 → 3)-GalNAc; and phosphoglycerol and phosphocholine residues which have not been previously observed together as functional groups on the same oligosaccharide. The successful third-generation approach leverages a first in class glycosylation of a phosphoglycerol-functionalized acceptor. To install the phosphocholine unit, a highly effective phosphocholine donor was synthesized.
Desymmetrization of glycerol derivatives with peptide-based acylation catalysts
Lewis, Chad A.,Sculimbrene, Bianca R.,Xu, Yingju,Miller, Scott J.
, p. 3021 - 3023 (2007/10/03)
(Chemical Equation Presented) Nucleophile-loaded peptides have been evaluated as catalysts for the desymmetrization of glycerol derivatives through an enantioselective acylation process. Enantiomeric excesses of up to 97% have been obtained for the monoac
Hydrolases in organic synthesis: Preparation of enantiomerically pure compounds
Ader, U,Andersch, P,Berger, M,Goergens, U,Seemayer, R,Schneider, M
, p. 145 - 150 (2007/10/02)
Esterhydrolases (Esterases, Lipases) are highly (chemo-, regio- and enantio-) selective biocatalysts for the transformation of racemic and achiral substrates into enantiomerically pure compounds.Numerous examples for their application in the preparation of synthetically useful chiral auxiliaries and building blocks for flavour compounds, pheromones and several pharmaceuticals including β-adrenergic blockers, antidepressants and ACE inhibitors are presented.
Enzymatic preparation of acylglycerols of high optical purity
Ghisalba, Oreste,Lattmann, Rene,Gygax, Daniel
, p. 263 - 264 (2007/10/02)
(S)-3-O-acyl-2-O-benzylglycerols with an optical purity of > 98percent ee can be prepared in high yield by transesterification in a solvent free system using Pseudomonas fluorescens lipase.
Efficient Lipase-Catalyzed Synthesis of Chiral Glycerol Derivatives
Murata, Masakazu,Terao, Yoshiyasu,Achiwa, Kazuo,Nishio, Tishiyuki,Seto, Kazumaro
, p. 2670 - 2672 (2007/10/02)
Efficient asymmetric syntheses of glycerol derivatives were achieved by lipase-catalyzed transesterification. 2-O-Substituted glycerol was enzymatically esterified with acetic acid or acetate in an organic medium to afford an optically active monoester.In
Lipase-Catalyzed Irreversible Transesterification for Preparative Synthesis of Chiral Glycerol Derivatives
Wang, Yi-Fong,Wong, Chi-Huey
, p. 3127 - 3129 (2007/10/02)
An irreversible, lipase-catalysed transesterification using enol ester as an acylating agent has been developed for preparative enantioselective acylation of meso-1,3-diols.
HIGHLY EFFICIENT LIPASE-CATALYZED ASYMMETRIC SYNTHESIS OF CHIRAL GLYCEROL DERIVATIVES LEADING TO PRACTICAL SYNTHESIS OF (S)-PROPRANOLOL
Terao, Yoshiyasu,Murata, Masakazu,Achiwa, Kazuo,Nishio, Toshiyuki,Akamtsu, Minoru,Kamimura, Minoru
, p. 5173 - 5176 (2007/10/02)
Efficient asymmetric synthesis of chiral glycerol derivatives was realized by lipase-catalyzed reaction in organic medium and its application for synthesis of (S)-propranolol was demostrated.
Enzymatic Differentiation of the Enantiotopic Hydroxymethyl Groups of Glycerol; Synthesis of Chiral Building Blocks
Breitgoff, Detlev,Laumen, Kurt,Schneider, Manfred P.
, p. 1523 - 1524 (2007/10/02)
The prochiral (3b), derived from glycerol, was transformed by enantioselective, enzymatic hydrolysis into the central chiral building block (R)-(4) of high enantiometric purity, which was further elaborated into a variety of chiral building blocks with th
