An expedient stereoselective synthesis of sialyl-α-(2->3)-TF-Ser/Thr building block derivatives for solid-phase glycopeptide synthesis

J. Satyanarayana; T. L. Gururaja; G. A. Naganagowda; S. Narasimhamurthy; M. J. Levine

An expedient stereoselective synthesis of sialyl-α-(2->3)-TF-Ser/Thr building block derivatives for solid-phase glycopeptide synthesis

J. Satyanarayana
, T. L. Gururaja
, G. A. Naganagowda
, S. Narasimhamurthy
, M. J. Levine

Department of Oral Biology

SUNY Buffalo

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

1 Scopus citations

Abstract

Stereoselective synthesis of Fmoc-Ser/Thr-OPfp derivatives O- glycosidically α-linked to fully protected α-D-NeuAc-(2->3)-β-D-Gal-(l- >3)-α-D-GalN₃ (1-2) is described for the first time starting from methyl- 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(l->3)-4,6-O-benzylidene-2- azido-2-deoxy-β-D-galactopyranoside (4). Conversion of sialyl-trisaccharide derivative (12) to its bromide (13) with TiBr₄ followed by silver perchlorate promoted glycosylation with Fmoc-Ser/Thr-OPfp (14) afforded the target building blocks in good yields.

Original language	English
Pages (from-to)	297-304
Number of pages	8
Journal	Carbohydrate Letters
Volume	3
Issue number	5
State	Published - 1999

Keywords

Glycoamino acids
Glycopeptides
Human salivary mucin (MUC7)
N-acetylneuraminic acid
O-glycosylation
Sialyl-α-(2->3)-TF antigens

Cite this

@article{7ceb7300f3b641f2bd54c115edb0e84e,

title = "An expedient stereoselective synthesis of sialyl-α-(2->3)-TF-Ser/Thr building block derivatives for solid-phase glycopeptide synthesis",

abstract = "Stereoselective synthesis of Fmoc-Ser/Thr-OPfp derivatives O- glycosidically α-linked to fully protected α-D-NeuAc-(2->3)-β-D-Gal-(l- >3)-α-D-GalN3 (1-2) is described for the first time starting from methyl- 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(l->3)-4,6-O-benzylidene-2- azido-2-deoxy-β-D-galactopyranoside (4). Conversion of sialyl-trisaccharide derivative (12) to its bromide (13) with TiBr4 followed by silver perchlorate promoted glycosylation with Fmoc-Ser/Thr-OPfp (14) afforded the target building blocks in good yields.",

keywords = "Glycoamino acids, Glycopeptides, Human salivary mucin (MUC7), N-acetylneuraminic acid, O-glycosylation, Sialyl-α-(2->3)-TF antigens",

author = "J. Satyanarayana and Gururaja, \{T. L.\} and Naganagowda, \{G. A.\} and S. Narasimhamurthy and Levine, \{M. J.\}",

year = "1999",

language = "English",

volume = "3",

pages = "297--304",

journal = "Carbohydrate Letters",

issn = "1073-5070",

publisher = "Harwood Academic Publishers",

number = "5",

}

TY - JOUR

T1 - An expedient stereoselective synthesis of sialyl-α-(2->3)-TF-Ser/Thr building block derivatives for solid-phase glycopeptide synthesis

AU - Satyanarayana, J.

AU - Gururaja, T. L.

AU - Naganagowda, G. A.

AU - Narasimhamurthy, S.

AU - Levine, M. J.

PY - 1999

Y1 - 1999

N2 - Stereoselective synthesis of Fmoc-Ser/Thr-OPfp derivatives O- glycosidically α-linked to fully protected α-D-NeuAc-(2->3)-β-D-Gal-(l- >3)-α-D-GalN3 (1-2) is described for the first time starting from methyl- 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(l->3)-4,6-O-benzylidene-2- azido-2-deoxy-β-D-galactopyranoside (4). Conversion of sialyl-trisaccharide derivative (12) to its bromide (13) with TiBr4 followed by silver perchlorate promoted glycosylation with Fmoc-Ser/Thr-OPfp (14) afforded the target building blocks in good yields.

AB - Stereoselective synthesis of Fmoc-Ser/Thr-OPfp derivatives O- glycosidically α-linked to fully protected α-D-NeuAc-(2->3)-β-D-Gal-(l- >3)-α-D-GalN3 (1-2) is described for the first time starting from methyl- 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(l->3)-4,6-O-benzylidene-2- azido-2-deoxy-β-D-galactopyranoside (4). Conversion of sialyl-trisaccharide derivative (12) to its bromide (13) with TiBr4 followed by silver perchlorate promoted glycosylation with Fmoc-Ser/Thr-OPfp (14) afforded the target building blocks in good yields.

KW - Glycoamino acids

KW - Glycopeptides

KW - Human salivary mucin (MUC7)

KW - N-acetylneuraminic acid

KW - O-glycosylation

KW - Sialyl-α-(2->3)-TF antigens

UR - https://www.scopus.com/pages/publications/0033431634

M3 - Article

AN - SCOPUS:0033431634

SN - 1073-5070

VL - 3

SP - 297

EP - 304

JO - Carbohydrate Letters

JF - Carbohydrate Letters

IS - 5

ER -

An expedient stereoselective synthesis of sialyl-α-(2->3)-TF-Ser/Thr building block derivatives for solid-phase glycopeptide synthesis

Abstract

Keywords

Other files and links

Fingerprint

Cite this