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Synthesis of the complete series of mono acetates of N-acetyl-D-neuraminic acid

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Synthesis of the complete series of mono acetates of N-acetyl-D-neuraminic acid. / Clarke, Paul A; Mistry, Nimesh; Thomas, Gavin H.

In: Organic & biomolecular chemistry, Vol. 10, No. 3, 21.01.2012, p. 529-35.

Research output: Contribution to journalArticlepeer-review

Harvard

Clarke, PA, Mistry, N & Thomas, GH 2012, 'Synthesis of the complete series of mono acetates of N-acetyl-D-neuraminic acid', Organic & biomolecular chemistry, vol. 10, no. 3, pp. 529-35. https://doi.org/10.1039/c1ob06348k

APA

Clarke, P. A., Mistry, N., & Thomas, G. H. (2012). Synthesis of the complete series of mono acetates of N-acetyl-D-neuraminic acid. Organic & biomolecular chemistry, 10(3), 529-35. https://doi.org/10.1039/c1ob06348k

Vancouver

Clarke PA, Mistry N, Thomas GH. Synthesis of the complete series of mono acetates of N-acetyl-D-neuraminic acid. Organic & biomolecular chemistry. 2012 Jan 21;10(3):529-35. https://doi.org/10.1039/c1ob06348k

Author

Clarke, Paul A ; Mistry, Nimesh ; Thomas, Gavin H. / Synthesis of the complete series of mono acetates of N-acetyl-D-neuraminic acid. In: Organic & biomolecular chemistry. 2012 ; Vol. 10, No. 3. pp. 529-35.

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@article{2f770cb9f20649daad2ab2d88677e929,
title = "Synthesis of the complete series of mono acetates of N-acetyl-D-neuraminic acid",
abstract = "The short syntheses of each of the mono-acetates of N-acetyl-D-neuraminic acid are reported. These are important molecules for studying the mechanism and function of enzymes which utilise Neu5Ac as a substrate. However, until now these molecules were not available as pure compounds and instead had to be studied as mixtures. Neu4,5Ac(2) and Neu5,8Ac(2) were synthesised from a common precursor in 2 and 4 steps respectively, while Neu2,4Ac(2) and Neu5,7Ac(2) were synthesised in 3 and 4 steps respectively from another common precursor. Both precursors could be easily prepared in 3 steps from Neu5Ac itself. Importantly, no scrambling of the anomeric stereochemistry was detected throughout the course of these syntheses.",
author = "Clarke, {Paul A} and Nimesh Mistry and Thomas, {Gavin H}",
year = "2012",
month = jan,
day = "21",
doi = "10.1039/c1ob06348k",
language = "English",
volume = "10",
pages = "529--35",
journal = "Organic & biomolecular chemistry",
issn = "1477-0539",
number = "3",

}

RIS (suitable for import to EndNote) - Download

TY - JOUR

T1 - Synthesis of the complete series of mono acetates of N-acetyl-D-neuraminic acid

AU - Clarke, Paul A

AU - Mistry, Nimesh

AU - Thomas, Gavin H

PY - 2012/1/21

Y1 - 2012/1/21

N2 - The short syntheses of each of the mono-acetates of N-acetyl-D-neuraminic acid are reported. These are important molecules for studying the mechanism and function of enzymes which utilise Neu5Ac as a substrate. However, until now these molecules were not available as pure compounds and instead had to be studied as mixtures. Neu4,5Ac(2) and Neu5,8Ac(2) were synthesised from a common precursor in 2 and 4 steps respectively, while Neu2,4Ac(2) and Neu5,7Ac(2) were synthesised in 3 and 4 steps respectively from another common precursor. Both precursors could be easily prepared in 3 steps from Neu5Ac itself. Importantly, no scrambling of the anomeric stereochemistry was detected throughout the course of these syntheses.

AB - The short syntheses of each of the mono-acetates of N-acetyl-D-neuraminic acid are reported. These are important molecules for studying the mechanism and function of enzymes which utilise Neu5Ac as a substrate. However, until now these molecules were not available as pure compounds and instead had to be studied as mixtures. Neu4,5Ac(2) and Neu5,8Ac(2) were synthesised from a common precursor in 2 and 4 steps respectively, while Neu2,4Ac(2) and Neu5,7Ac(2) were synthesised in 3 and 4 steps respectively from another common precursor. Both precursors could be easily prepared in 3 steps from Neu5Ac itself. Importantly, no scrambling of the anomeric stereochemistry was detected throughout the course of these syntheses.

UR - http://www.scopus.com/inward/record.url?scp=84055214190&partnerID=8YFLogxK

U2 - 10.1039/c1ob06348k

DO - 10.1039/c1ob06348k

M3 - Article

C2 - 22095310

VL - 10

SP - 529

EP - 535

JO - Organic & biomolecular chemistry

JF - Organic & biomolecular chemistry

SN - 1477-0539

IS - 3

ER -