Iodine-mediated glycosylation en route to mucin-related glyco-aminoacids and glycopeptides

Tiina S. Kärkkäinen; K. P. Ravindranathan Kartha; Derek MacMillan; Robert A. Field

doi:10.1016/j.carres.2008.03.034

Iodine-mediated glycosylation en route to mucin-related glyco-aminoacids and glycopeptides

Tiina S. Kärkkäinen, K. P. Ravindranathan Kartha, Derek MacMillan, Robert A. Field

School of Biological Sciences

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

16 Citations (Scopus)

Abstract

The use of iodine-DDQ as a promoter for glycosylation of Fmoc-Ser-OBn and Fmoc-Thr-OBn with phenylseleno 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-d-galactopyranoside in toluene-dioxane gave 49% and 73% yields, respectively, of the corresponding α-glycosides as the sole glycoside products. Reductive acetylation of the azide groups and cleavage of the benzyl esters by hydrogenolysis gave building blocks that were used in solid-phase synthesis to prepare triglycosylated tetrapeptides (Ac₃GalNAc-α-Ser)₃-Gly and (Ac₃GalNAc-α-Thr)₃-Gly in 27% and 49% overall yield, respectively.

Original language	English
Pages (from-to)	1830-1834
Number of pages	5
Journal	Carbohydrate Research
Volume	343
Issue number	10-11
Early online date	7 Apr 2008
DOIs	https://doi.org/10.1016/j.carres.2008.03.034
Publication status	Published - 21 Jul 2008

Keywords

Aminoacid
Glycopeptide
Glycosylation
Iodine-DDQ
Mucin
Phenyl selenoglycoside

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10.1016/j.carres.2008.03.034

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title = "Iodine-mediated glycosylation en route to mucin-related glyco-aminoacids and glycopeptides",

abstract = "The use of iodine-DDQ as a promoter for glycosylation of Fmoc-Ser-OBn and Fmoc-Thr-OBn with phenylseleno 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-d-galactopyranoside in toluene-dioxane gave 49% and 73% yields, respectively, of the corresponding α-glycosides as the sole glycoside products. Reductive acetylation of the azide groups and cleavage of the benzyl esters by hydrogenolysis gave building blocks that were used in solid-phase synthesis to prepare triglycosylated tetrapeptides (Ac3GalNAc-α-Ser)3-Gly and (Ac3GalNAc-α-Thr)3-Gly in 27% and 49% overall yield, respectively.",

keywords = "Aminoacid, Glycopeptide, Glycosylation, Iodine-DDQ, Mucin, Phenyl selenoglycoside",

author = "K{\"a}rkk{\"a}inen, {Tiina S.} and Kartha, {K. P. Ravindranathan} and Derek MacMillan and Field, {Robert A.}",

note = "Funding Information: This work was supported by the Association for International Cancer Research (studentship to T.S.K.) and the Royal Society (University Research Fellowship to D.M.). We thank the EPSRC Mass Spectrometry Service Centre, Swansea, for invaluable support. ",

year = "2008",

month = jul,

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doi = "10.1016/j.carres.2008.03.034",

language = "English",

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T1 - Iodine-mediated glycosylation en route to mucin-related glyco-aminoacids and glycopeptides

AU - Kärkkäinen, Tiina S.

AU - Kartha, K. P. Ravindranathan

AU - MacMillan, Derek

AU - Field, Robert A.

N1 - Funding Information: This work was supported by the Association for International Cancer Research (studentship to T.S.K.) and the Royal Society (University Research Fellowship to D.M.). We thank the EPSRC Mass Spectrometry Service Centre, Swansea, for invaluable support.

PY - 2008/7/21

Y1 - 2008/7/21

N2 - The use of iodine-DDQ as a promoter for glycosylation of Fmoc-Ser-OBn and Fmoc-Thr-OBn with phenylseleno 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-d-galactopyranoside in toluene-dioxane gave 49% and 73% yields, respectively, of the corresponding α-glycosides as the sole glycoside products. Reductive acetylation of the azide groups and cleavage of the benzyl esters by hydrogenolysis gave building blocks that were used in solid-phase synthesis to prepare triglycosylated tetrapeptides (Ac3GalNAc-α-Ser)3-Gly and (Ac3GalNAc-α-Thr)3-Gly in 27% and 49% overall yield, respectively.

AB - The use of iodine-DDQ as a promoter for glycosylation of Fmoc-Ser-OBn and Fmoc-Thr-OBn with phenylseleno 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-d-galactopyranoside in toluene-dioxane gave 49% and 73% yields, respectively, of the corresponding α-glycosides as the sole glycoside products. Reductive acetylation of the azide groups and cleavage of the benzyl esters by hydrogenolysis gave building blocks that were used in solid-phase synthesis to prepare triglycosylated tetrapeptides (Ac3GalNAc-α-Ser)3-Gly and (Ac3GalNAc-α-Thr)3-Gly in 27% and 49% overall yield, respectively.

KW - Aminoacid

KW - Glycopeptide

KW - Glycosylation

KW - Iodine-DDQ

KW - Mucin

KW - Phenyl selenoglycoside

UR - http://www.scopus.com/inward/record.url?scp=46549085738&partnerID=8YFLogxK

U2 - 10.1016/j.carres.2008.03.034

DO - 10.1016/j.carres.2008.03.034

M3 - Article

C2 - 18439574

AN - SCOPUS:46549085738

VL - 343

SP - 1830

EP - 1834

JO - Carbohydrate Research

JF - Carbohydrate Research

SN - 0008-6215

IS - 10-11

ER -

Iodine-mediated glycosylation en route to mucin-related glyco-aminoacids and glycopeptides

Abstract

Keywords

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