Literature DB >> 20622936

Synthesis of Differentially Protected myo- and chiro-Inositols from D-Xylose; Stereoselectivity in Intramolecular SmI(2)-Promoted Pinacol Reactions.

Giovanni Luchetti1, Kejia Ding, Alexander Kornienko, Marc d'Alarcao.   

Abstract

Methods for the enantioselective conversion of D-xylose to differentially protected myo-inositol and L-chiro-inositol have been developed. The key transformation is a highly diastereoselective intramolecular SmI(2)-promoted pinacol coupling. The stereoselectivity was extremely dependent on the conditions, suggesting a change in mechanism. Preliminary mechanistic experiments and possible explanations for this behavior are discussed.

Entities:  

Year:  2008        PMID： 20622936      PMCID： PMC2900855          DOI： 10.1055/s-2008-1067259

Source DB:  PubMed          Journal:  Synthesis (Stuttg)        ISSN： 0039-7881            Impact factor:   3.157


  27 in total

Review 1.  Insulin second messengers.

Authors:  P Strålfors
Journal:  Bioessays       Date:  1997-04       Impact factor: 4.345

2.  Fagopyritol B1, O-alpha-D-galactopyranosyl-(1-->2)-D-chiro-inositol, a galactosyl cyclitol in maturing buckwheat seeds associated with desiccation tolerance.

Authors:  M Horbowicz; P Brenac; R L Obendorf
Journal:  Planta       Date:  1998-05       Impact factor: 4.116

Review 3.  Inositol trisphosphate and diacylglycerol: two interacting second messengers.

Authors:  M J Berridge
Journal:  Annu Rev Biochem       Date:  1987       Impact factor: 23.643

4.  Synthesis of inositol glycan cyclic phosphates.

Authors:  C H Jaworek; S Iacobucci; P Calias; M d'Alarcao
Journal:  Carbohydr Res       Date:  2001-04-23       Impact factor: 2.104

5.  Design and synthesis of inositolphosphoglycan putative insulin mediators.

Authors:  Javier López-Prados; Félix Cuevas; Niels-Christian Reichardt; José-Luis de Paz; Ezequiel Q Morales; Manuel Martín-Lomas
Journal:  Org Biomol Chem       Date:  2005-02-02       Impact factor: 3.876

6.  Chemical validation of GPI biosynthesis as a drug target against African sleeping sickness.

Authors:  Terry K Smith; Arthur Crossman; John S Brimacombe; Michael A J Ferguson
Journal:  EMBO J       Date:  2004-11-04       Impact factor: 11.598

7.  Stereoselective total synthesis of the glycosyl phosphatidylinositol (GPI) anchor of Trypanosoma brucei.

Authors:  C Murakata; T Ogawa
Journal:  Carbohydr Res       Date:  1992-11-04       Impact factor: 2.104

8.  Structure-activity relationship of synthetic phosphoinositolglycans mimicking metabolic insulin action.

Authors:  W Frick; A Bauer; J Bauer; S Wied; G Müller
Journal:  Biochemistry       Date:  1998-09-22       Impact factor: 3.162

9.  Convergent synthesis of a GPI containing an acylated inositol.

Authors:  Jie Xue; Zhongwu Guo
Journal:  J Am Chem Soc       Date:  2003-12-31       Impact factor: 15.419

Review 10.  The structure, biosynthesis and functions of glycosylphosphatidylinositol anchors, and the contributions of trypanosome research.

Authors:  M A Ferguson
Journal:  J Cell Sci       Date:  1999-09       Impact factor: 5.285
View more
  1 in total

Review 1.  The "Other" Inositols and Their Phosphates: Synthesis, Biology, and Medicine (with Recent Advances in myo-Inositol Chemistry).

Authors:  Mark P Thomas; Stephen J Mills; Barry V L Potter
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-22       Impact factor: 15.336
  1 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.