Literature DB >> 25800650

Stereoselective synthesis of UDP-2-(2-ketopropyl)galactose aided by di-tert-butylsilylene protecting group.

Yasuharu Sakamoto1, Tsuyoshi Ohta2, Yukishige Ito3,4.   

Abstract

UDP-2-(2-ketopropyl)galactose (1) has been utilized as a valuable probe for profiling proteins modified by O-GlcNAc. In this work, we developed a protocol for efficient synthesis of 1. Thus, 2-methallylgalactose derivative 11, a synthetic intermediate for the compound 1, was prepared by stereoselective iodination and methallylation at C-2 position, through exploitation of 4,6-O-di-tert-butylsilylene protecting group.

Entities:  

Keywords:  Di-tert-butylsilylene; Galactose derivative; Iodination; Radical methallylation; Stereoselective synthesis

Mesh：

Substances：

Year:  2015        PMID： 25800650     DOI： 10.1007/s10719-015-9581-y

Source DB:  PubMed          Journal:  Glycoconj J        ISSN： 0282-0080            Impact factor:   2.916


  23 in total

1.  Ketone isosteres of 2-N-acetamidosugars as substrates for metabolic cell surface engineering.

Authors:  H C Hang; C R Bertozzi
Journal:  J Am Chem Soc       Date:  2001-02-14       Impact factor: 15.419

Review 2.  The emerging significance of O-GlcNAc in cellular regulation.

Authors:  Natasha E Zachara; Gerald W Hart
Journal:  Chem Rev       Date:  2002-02       Impact factor: 60.622

3.  Beta-N-acetylglucosamine (O-GlcNAc) is part of the histone code.

Authors:  Kaoru Sakabe; Zihao Wang; Gerald W Hart
Journal:  Proc Natl Acad Sci U S A       Date:  2010-11-02       Impact factor: 11.205

4.  β-N-Acetylglucosamine (O-GlcNAc) is a novel regulator of mitosis-specific phosphorylations on histone H3.

Authors:  Jerry J Fong; Brenda L Nguyen; Robert Bridger; Estela E Medrano; Lance Wells; Shujuan Pan; Richard N Sifers
Journal:  J Biol Chem       Date:  2012-02-27       Impact factor: 5.157

5.  Enzymatic addition of O-GlcNAc to nuclear and cytoplasmic proteins. Identification of a uridine diphospho-N-acetylglucosamine:peptide beta-N-acetylglucosaminyltransferase.

Authors:  R S Haltiwanger; G D Holt; G W Hart
Journal:  J Biol Chem       Date:  1990-02-15       Impact factor: 5.157

6.  Improved synthesis of UDP-2-(2-ketopropyl)galactose and a first synthesis of UDP-2-(2-ketopropyl)glucose for the site-specific linking of biomolecules via modified glycan residues using glycosyltransferases.

Authors:  Andrés E Dulcey; Pradman K Qasba; Jeffrey Lamb; Gary L Griffiths
Journal:  Tetrahedron       Date:  2011-03-18       Impact factor: 2.457

7.  Modification of histones by sugar β-N-acetylglucosamine (GlcNAc) occurs on multiple residues, including histone H3 serine 10, and is cell cycle-regulated.

Authors:  Suisheng Zhang; Kevin Roche; Heinz-Peter Nasheuer; Noel Francis Lowndes
Journal:  J Biol Chem       Date:  2011-09-06       Impact factor: 5.157

8.  Purification and characterization of an O-GlcNAc selective N-acetyl-beta-D-glucosaminidase from rat spleen cytosol.

Authors:  D L Dong; G W Hart
Journal:  J Biol Chem       Date:  1994-07-29       Impact factor: 5.157

Review 9.  Cycling of O-linked beta-N-acetylglucosamine on nucleocytoplasmic proteins.

Authors:  Gerald W Hart; Michael P Housley; Chad Slawson
Journal:  Nature       Date:  2007-04-26       Impact factor: 49.962

10.  Dynamic O-GlcNAcylation of the small heat shock protein alpha B-crystallin.

Authors:  E P Roquemore; M R Chevrier; R J Cotter; G W Hart
Journal:  Biochemistry       Date:  1996-03-19       Impact factor: 3.162
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