Stereocontrolled and Convergent Entry to CF2-Sialosides:  Synthesis of CF2-Linked Ganglioside GM4

Hirai, Go; Watanabe, Tôru; Yamaguchi, Kazunori; Miyagi, Taeko; Sodeoka, Mikiko

doi:10.1021/ja075738w

Cited by 66 publications

(52 citation statements)

References 33 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Unique structure (Hada, et al, 2007) CF 2 (Hirai, et al, 2007) (Hada, et al, 2008b) Glycosphingolipids from Mucor hiemalis TOF, FAB Synthesis of compounds with Gal-α-(1→6)-Gal linkages (Hada, et al, 2008a) GM1, GM2, GM3 probes TOF (CHCA) Ceramide replaced by glucose. For probes for microarray ) Lyso-GM3, monomer, dimer and multimer TOF Synthesis and effect on epidermal growth factor-induced receptor tyrosine kinase (Murozuka, et al, 2007) 6′-NeuAc-GM2 and α-GalNAc-GM2 TOF (CHCA)…”

Section: Peptidoglycansmentioning

confidence: 99%

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

Harvey

2011

Mass Spectrometry Reviews

View full text Add to dashboard Cite

This review is the fifth update of the original review, published in 1999, on the application of MALDI mass spectrometry to the analysis of carbohydrates and glycoconjugates and brings coverage of the literature to the end of 2008. The first section of the review covers fundamental studies, fragmentation of carbohydrate ions, use of derivatives and new software developments for analysis of carbohydrate spectra. Among newer areas of method development are glycan arrays, MALDI imaging and the use of ion mobility spectrometry. The second section of the review discusses applications of MALDI MS to the analysis of different types of carbohydrate. Specific compound classes that are covered include carbohydrate polymers from plants, N- and O-linked glycans from glycoproteins, biopharmaceuticals, glycated proteins, glycolipids, glycosides and various other natural products. There is a short section on the use of MALDI mass spectrometry for the study of enzymes involved in glycan processing and a section on the use of MALDI MS to monitor products of the chemical synthesis of carbohydrates with emphasis on carbohydrate-protein complexes and glycodendrimers. Corresponding analyses by electrospray ionization now appear to outnumber those performed by MALDI and the amount of literature makes a comprehensive review on this technique impractical. However, most of the work relating to sample preparation and glycan synthesis is equally relevant to electrospray and, consequently, those proposing analyses by electrospray should also find material in this review of interest.

show abstract

Section: Peptidoglycansmentioning

confidence: 99%

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

Harvey

2011

Mass Spectrometry Reviews

View full text Add to dashboard Cite

show abstract

“…The ability of synthetic chemists to construct desired glycoside bonds has progressed and has contributed to our understanding of the recognition mechanisms for receptor proteins and the development of enzyme inhibitors. [7][8][9][10] Sialylation is one of the most challenging reactions in carbohydrate chemistry and often proceeds with low yield and poor stereoselectivity. [11][12][13] In particular, the stereoselective synthesis of a-sialosides is complicated because sialic acid does not contain a neighboring C-3 functional group to direct the stereochemical outcome of the glycosylation.…”

Section: Introductionmentioning

confidence: 99%

Chemical approach for the syntheses of GM4 isomers with sialic acid to non-natural linkage positions on galactose

Kurimoto

Yamamura

Miyagawa

2015

Carbohydrate Research

View full text Add to dashboard Cite

“…1), a highly acidic pentabasic acid. Because of the "biostericity" and similar polarity of the CF 2 groups to the bridging oxygen atoms (3)(4)(5), this compound is a nonhydrolyzable analog of triphosphoric acid, albeit with lower pK a S (vide infra), a vital part of nucleotides containing both oxy-and deoxyriboses. It is important to emphasize that no other known (α,β),(β,γ)-bis-substituted triphosphate analog retains the "right" polarity and steric features of the natural triphosphate.…”

mentioning

confidence: 99%

Synthesis and biological evaluation of fluorinated deoxynucleotide analogs based on bis-(difluoromethylene)triphosphoric acid

Prakash

Zibinsky

Upton

et al. 2010

Proc. Natl. Acad. Sci. U.S.A.

View full text Add to dashboard Cite

It is difficult to overestimate the importance of nucleoside triphosphates in cellular chemistry: They are the building blocks for DNA and RNA and important sources of energy. Modifications of biologically important organic molecules with fluorine are of great interest to chemists and biologists because the size and electronegativity of the fluorine atom can be used to make defined structural alterations to biologically important molecules. Although the concept of nonhydrolyzable nucleotides has been around for some time, the progress in the area of modified triphosphates was limited by the lack of synthetic methods allowing to access bisCF 2 -substituted nucleotide analogs-one of the most interesting classes of nonhydrolyzable nucleotides. These compounds have "correct" polarity and the smallest possible steric perturbation compared to natural nucleotides. No other known nucleotides have these advantages, making bisCF 2 -substituted analogs unique. Herein, we report a concise route for the preparation of hitherto unknown highly acidic and polybasic bis(difluoromethylene)triphosphoric acid 1 using a phosphorous(III)/phosphorous(V) interconversion approach. The analog 1 compared to triphosphoric acid is enzymatically nonhydrolyzable due to substitution of two bridging oxygen atoms with CF 2 groups, maintaining minimal perturbations in steric bulkiness and overall polarity of the triphosphate polyanion. The fluorinated triphosphoric acid 1 was used for the preparation of the corresponding fluorinated deoxynucleotides (dNTPs). One of these dNTP analogs (dT) was demonstrated to fit into DNA polymerase beta (DNA pol β) binding pocket by obtaining a 2.5 Å resolution crystal structure of a ternary complex with the enzyme. Unexpected dominating effect of triphosphate∕Mg 2þ interaction over Watson-Crick hydrogen bonding was found and discussed.DNA polymerase beta | nonhydrolyzable nucleotides | fluorinated triphosphate | pentabasic acid | isopolarity and bioisotericity

show abstract

Stereocontrolled and Convergent Entry to CF₂-Sialosides: Synthesis of CF₂-Linked Ganglioside GM4

Cited by 66 publications

References 33 publications

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

Chemical approach for the syntheses of GM4 isomers with sialic acid to non-natural linkage positions on galactose

Synthesis and biological evaluation of fluorinated deoxynucleotide analogs based on bis-(difluoromethylene)triphosphoric acid

Contact Info

Product

Resources

About