Synthesis of Sugar Nucleotides by Application of Phosphoramidites

H. Gold; P. van Delft; N. Meeuwenoord; J.D.C. Codee; D.V. Filippov; G. Eggink; H.S. Overkleeft; G.A. van der Marel

doi:10.1021/jo802021t

Synthesis of Sugar Nucleotides by Application of Phosphoramidites

H. Gold, P. van Delft, N. Meeuwenoord, J.D.C. Codee, D.V. Filippov, G. Eggink, H.S. Overkleeft, G.A. van der Marel

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Abstract

new method for the construction of pyrophosphates is reported based on the coupling of a sugar phosphate and a nucleoside phosphoramidite. The in situ formed phosphate¿phosphite intermediate was subsequently oxidized with tBuOOH. Three UDP-N-acetylglucosamine derivatives were prepared using this one-pot procedure in good yields.

Original language	English
Pages (from-to)	9458-9460
Journal	Journal of Organic Chemistry
Volume	73
Issue number	23
DOIs	https://doi.org/10.1021/jo802021t
Publication status	Published - 2008

Keywords

potential chain-terminators
udp-glcnac analogs
chemical-synthesis
nucleoside polyphosphates
efficient synthesis
gdp-fucose
derivatives
glycosyltransferases
biosynthesis
galactose

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10.1021/jo802021t

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title = "Synthesis of Sugar Nucleotides by Application of Phosphoramidites",

abstract = "new method for the construction of pyrophosphates is reported based on the coupling of a sugar phosphate and a nucleoside phosphoramidite. The in situ formed phosphate¿phosphite intermediate was subsequently oxidized with tBuOOH. Three UDP-N-acetylglucosamine derivatives were prepared using this one-pot procedure in good yields.",

keywords = "potential chain-terminators, udp-glcnac analogs, chemical-synthesis, nucleoside polyphosphates, efficient synthesis, gdp-fucose, derivatives, glycosyltransferases, biosynthesis, galactose",

author = "H. Gold and {van Delft}, P. and N. Meeuwenoord and J.D.C. Codee and D.V. Filippov and G. Eggink and H.S. Overkleeft and {van der Marel}, G.A.",

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doi = "10.1021/jo802021t",

language = "English",

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journal = "Journal of Organic Chemistry",

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TY - JOUR

T1 - Synthesis of Sugar Nucleotides by Application of Phosphoramidites

AU - Gold, H.

AU - van Delft, P.

AU - Meeuwenoord, N.

AU - Codee, J.D.C.

AU - Filippov, D.V.

AU - Eggink, G.

AU - Overkleeft, H.S.

AU - van der Marel, G.A.

PY - 2008

Y1 - 2008

N2 - new method for the construction of pyrophosphates is reported based on the coupling of a sugar phosphate and a nucleoside phosphoramidite. The in situ formed phosphate¿phosphite intermediate was subsequently oxidized with tBuOOH. Three UDP-N-acetylglucosamine derivatives were prepared using this one-pot procedure in good yields.

AB - new method for the construction of pyrophosphates is reported based on the coupling of a sugar phosphate and a nucleoside phosphoramidite. The in situ formed phosphate¿phosphite intermediate was subsequently oxidized with tBuOOH. Three UDP-N-acetylglucosamine derivatives were prepared using this one-pot procedure in good yields.

KW - potential chain-terminators

KW - udp-glcnac analogs

KW - chemical-synthesis

KW - nucleoside polyphosphates

KW - efficient synthesis

KW - gdp-fucose

KW - derivatives

KW - glycosyltransferases

KW - biosynthesis

KW - galactose

U2 - 10.1021/jo802021t

DO - 10.1021/jo802021t

M3 - Article

SN - 0022-3263

VL - 73

SP - 9458

EP - 9460

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 23

ER -

Synthesis of Sugar Nucleotides by Application of Phosphoramidites

Abstract

Keywords

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