Literature DB >> 12931973

Nonenzymatic peptide-based catalytic asymmetric phosphorylation of inositol derivatives.

Bianca R Sculimbrene1, Adam J Morgan, Scott J Miller.   

Abstract

The ability to use small peptides as catalysts for asymmetric phosphorylation provides opportunities for rapid syntheses of phosphate-containing compounds and natural products. This short review outlines the genesis of this concept and its reduction to practice in the context of concise syntheses of the enantiomeric D-I-1P and D-I-3P targets. The implications for the development of additional site-selective catalysts are discussed.

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Year:  2003        PMID: 12931973     DOI: 10.1039/b304015c

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  11 in total

1.  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.

Authors:  Christina M Longo; Yang Wei; Mary F Roberts; Scott J Miller
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

2.  Structure and Reactivity of Highly Twisted N-Acylimidazoles.

Authors:  Elizabeth A Stone; Brandon Q Mercado; Scott J Miller
Journal:  Org Lett       Date:  2019-03-12       Impact factor: 6.005

3.  Catalyst-Dependent Syntheses of Phosphatidylinositol-5 Phosphate-DiC8 and its Enantiomer.

Authors:  Katherine J Kayser-Bricker; Peter A Jordan; Scott J Miller
Journal:  Tetrahedron       Date:  2008-07-14       Impact factor: 2.457

Review 4.  Chemo- and site-selective derivatizations of natural products enabling biological studies.

Authors:  Omar Robles; Daniel Romo
Journal:  Nat Prod Rep       Date:  2014-03       Impact factor: 13.423

5.  Perdeuterated and 13C-enriched myo-inositol for DNP assisted monitoring of enzymatic phosphorylation by inositol-3-kinase.

Authors:  M J Moure; Y Zhuo; G J Boons; J H Prestegard
Journal:  Chem Commun (Camb)       Date:  2017-11-16       Impact factor: 6.222

Review 6.  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

7.  Asymmetric catalysis at a distance: catalytic, site-selective phosphorylation of teicoplanin.

Authors:  Sunkyu Han; Scott J Miller
Journal:  J Am Chem Soc       Date:  2013-08-07       Impact factor: 15.419

8.  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

9.  Site-selective catalysis of phenyl thionoformate transfer as a tool for regioselective deoxygenation of polyols.

Authors:  María Sanchez-Roselló; Angela L A Puchlopek; Adam J Morgan; Scott J Miller
Journal:  J Org Chem       Date:  2008-01-30       Impact factor: 4.354

10.  X-ray crystal structure of teicoplanin A₂-2 bound to a catalytic peptide sequence via the carrier protein strategy.

Authors:  Sunkyu Han; Binh V Le; Holly S Hajare; Richard H G Baxter; Scott J Miller
Journal:  J Org Chem       Date:  2014-09-02       Impact factor: 4.354

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