Literature DB >> 19425028

Asymmetric Syntheses of L,L- and L,D-di-myo-inositol-1,1'-phosphate and their behavior as stabilizers of enzyme activity at extreme temperatures.

Christina M Longo1, Yang Wei, Mary F Roberts, Scott J Miller.   

Abstract

The big "DIP"per: The preparation of both l,l-DIP and l,d-DIP (see structures) involves a complex case of double asymmetric induction in the key step of the synthesis. The differential ability of each isomer to contribute to thermoprotection in the context of a key enzyme has been assessed and both isomers of DIP are shown to possess biological activity.

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Year:  2009        PMID： 19425028      PMCID： PMC2854022          DOI： 10.1002/anie.200900480

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  14 in total

1.  Discovery of a catalytic asymmetric phosphorylation through selection of a minimal kinase mimic: a concise total synthesis of D-myo-inositol-1-phosphate.

Authors:  B R Sculimbrene; S J Miller
Journal:  J Am Chem Soc       Date:  2001-10-17       Impact factor: 15.419

2.  Nonenzymatic peptide-based catalytic asymmetric phosphorylation of inositol derivatives.

Authors:  Bianca R Sculimbrene; Adam J Morgan; Scott J Miller
Journal:  Chem Commun (Camb)       Date:  2003-08-07       Impact factor: 6.222

3.  Mix-and-heat benzylation of alcohols using a bench-stable pyridinium salt.

Authors:  Kevin W C Poon; Gregory B Dudley
Journal:  J Org Chem       Date:  2006-05-12       Impact factor: 4.354

Review 4.  Stress response by solute accumulation in archaea.

Authors:  Volker Müller; Regina Spanheimer; Helena Santos
Journal:  Curr Opin Microbiol       Date:  2005-10-26       Impact factor: 7.934

5.  Occurrence of 1-glyceryl-1-myo-inosityl phosphate in hyperthermophiles.

Authors:  Pedro Lamosa; Luís G Gonçalves; Marta V Rodrigues; Lígia O Martins; Neil D H Raven; Helena Santos
Journal:  Appl Environ Microbiol       Date:  2006-09       Impact factor: 4.792

6.  Accumulation of Mannosylglycerate and Di-myo-Inositol-Phosphate by Pyrococcus furiosus in Response to Salinity and Temperature.

Authors:  L O Martins; H Santos
Journal:  Appl Environ Microbiol       Date:  1995-09       Impact factor: 4.792

7.  Biosynthesis of Di-myo-inositol-1,1'-phosphate, a novel osmolyte in hyperthermophilic archaea.

Authors:  L Chen; E T Spiliotis; M F Roberts
Journal:  J Bacteriol       Date:  1998-08       Impact factor: 3.490

8.  The temperature dependence of the inositol monophosphatase Km correlates with accumulation of di-myo-inositol 1,1'-phosphate in Archaeoglobus fulgidus.

Authors:  Yanling Karen Wang; Adam Morgan; Kimberly Stieglitz; Boguslaw Stec; Benjamin Thompson; Scott J Miller; Mary F Roberts
Journal:  Biochemistry       Date:  2006-03-14       Impact factor: 3.162

9.  Genomic identification and in vitro reconstitution of a complete biosynthetic pathway for the osmolyte di-myo-inositol-phosphate.

Authors:  Dmitry A Rodionov; Oleg V Kurnasov; Boguslaw Stec; Yan Wang; Mary F Roberts; Andrei L Osterman
Journal:  Proc Natl Acad Sci U S A       Date:  2007-03-02       Impact factor: 11.205

10.  Bifunctional CTP:inositol-1-phosphate cytidylyltransferase/CDP-inositol:inositol-1-phosphate transferase, the key enzyme for di-myo-inositol-phosphate synthesis in several (hyper)thermophiles.

Authors:  Marta V Rodrigues; Nuno Borges; Mafalda Henriques; Pedro Lamosa; Rita Ventura; Chantal Fernandes; Nuno Empadinhas; Christopher Maycock; Milton S da Costa; Helena Santos
Journal:  J Bacteriol       Date:  2007-05-25       Impact factor: 3.490
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  7 in total

1.  Asymmetric phosphorylation through catalytic P(III) phosphoramidite transfer: enantioselective synthesis of D-myo-inositol-6-phosphate.

Authors:  Peter A Jordan; Katherine J Kayser-Bricker; Scott J Miller
Journal:  Proc Natl Acad Sci U S A       Date:  2010-05-03       Impact factor: 11.205

2.  Regiodivergent Glycosylations of 6-Deoxy-erythronolide B and Oleandomycin-Derived Macrolactones Enabled by Chiral Acid Catalysis.

Authors:  Jia-Hui Tay; Alonso J Argüelles; Matthew D DeMars; Paul M Zimmerman; David H Sherman; Pavel Nagorny
Journal:  J Am Chem Soc       Date:  2017-06-19       Impact factor: 15.419

Review 3.  Asymmetric Catalysis Mediated by Synthetic Peptides, Version 2.0: Expansion of Scope and Mechanisms.

Authors:  Anthony J Metrano; Alex J Chinn; Christopher R Shugrue; Elizabeth A Stone; Byoungmoo Kim; Scott J Miller
Journal:  Chem Rev       Date:  2020-09-24       Impact factor: 60.622

4.  A fully synthetic and biochemically validated phosphatidyl inositol-3-phosphate hapten via asymmetric synthesis and native chemical ligation.

Authors:  Brent D Chandler; Anne L Burkhardt; Klaudia Foley; Courtney Cullis; Denise Driscoll; Natalie Roy D'Amore; Scott J Miller
Journal:  J Am Chem Soc       Date:  2013-12-17       Impact factor: 15.419

5.  Catalytic asymmetric and stereodivergent oligonucleotide synthesis.

Authors:  Aaron L Featherston; Yongseok Kwon; Matthew M Pompeo; Oliver D Engl; David K Leahy; Scott J Miller
Journal:  Science       Date:  2021-02-12       Impact factor: 47.728

6.  Production of mannosylglycerate in Saccharomyces cerevisiae by metabolic engineering and bioprocess optimization.

Authors:  Cristiana Faria; Nuno Borges; Isabel Rocha; Helena Santos
Journal:  Microb Cell Fact       Date:  2018-11-16       Impact factor: 5.328

7.  Role of Mn2+ and compatible solutes in the radiation resistance of thermophilic bacteria and archaea.

Authors:  Kimberly M Webb; Jocelyne DiRuggiero
Journal:  Archaea       Date:  2012-11-14       Impact factor: 3.273
  7 in total

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