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

Research output: Contribution to journal › Article › Academic › peer-review

37 Citations (Scopus)

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

Access to Document

10.1021/jo802021t

Fingerprint Dive into the research topics of 'Synthesis of Sugar Nucleotides by Application of Phosphoramidites'. Together they form a unique fingerprint.

Cite this

@article{a116e1d66fbf42a4ad387ad4f85bffcd,

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.",

year = "2008",

doi = "10.1021/jo802021t",

language = "English",

volume = "73",

pages = "9458--9460",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "23",

}

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

VL - 73

SP - 9458

EP - 9460

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 23

ER -