Facile solid-phase synthesis of an antifreeze glycoprotein

Ping Hui Tseng; Weir Torn Jiaang; Meng Yang Chang; Shui Tein Chen

doi:10.1002/1521-3765(20010202)7:3<585::AID-CHEM585>3.3.CO;2-Y

Facile solid-phase synthesis of an antifreeze glycoprotein

Ping Hui Tseng, Weir Torn Jiaang, Meng Yang Chang, Shui Tein Chen

Institute of Biochemistry and Molecular Biology

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

37 Scopus citations

Abstract

The antifreeze glycoproteins (AFGPs) 1 are composed of a repeating tripeptide unit (Ala-Thr-Ala) in which the threonine residue is glycosylated with the disaccharide β-D-Gal-(1 → 3)-α-D-GalNAc. A new procedure for synthesizing AFGPs using Fmoc-(Ac₄-β-D-Gal-(1 → 3)-benzylidene-α-D-GalNAc)Thr-OH (10) as a building block has been developed. Total synthesis of the AFGPs (n=4, 8) in overall yields of 61% and 33%, respectively, has demonstrated the usefulness of the method. The synthetic AFGPs 1 (n=4, 8) showed a similar conformation to the native AFGPs in their circular dichroism spectra.

Original language	English
Pages (from-to)	585-590
Number of pages	6
Journal	Chemistry - A European Journal
Volume	7
Issue number	3
DOIs	https://doi.org/10.1002/1521-3765(20010202)7:3<585::AID-CHEM585>3.3.CO;2-Y
State	Published - 2 Feb 2001

Keywords

Antifreeze
Glycoproteins
Peptides
Solid-phase synthesis
T antigen

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10.1002/1521-3765(20010202)7:3<585::AID-CHEM585>3.3.CO;2-Y

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title = "Facile solid-phase synthesis of an antifreeze glycoprotein",

abstract = "The antifreeze glycoproteins (AFGPs) 1 are composed of a repeating tripeptide unit (Ala-Thr-Ala) in which the threonine residue is glycosylated with the disaccharide β-D-Gal-(1 → 3)-α-D-GalNAc. A new procedure for synthesizing AFGPs using Fmoc-(Ac4-β-D-Gal-(1 → 3)-benzylidene-α-D-GalNAc)Thr-OH (10) as a building block has been developed. Total synthesis of the AFGPs (n=4, 8) in overall yields of 61% and 33%, respectively, has demonstrated the usefulness of the method. The synthetic AFGPs 1 (n=4, 8) showed a similar conformation to the native AFGPs in their circular dichroism spectra.",

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AU - Tseng, Ping Hui

AU - Jiaang, Weir Torn

AU - Chang, Meng Yang

AU - Chen, Shui Tein

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Y1 - 2001/2/2

N2 - The antifreeze glycoproteins (AFGPs) 1 are composed of a repeating tripeptide unit (Ala-Thr-Ala) in which the threonine residue is glycosylated with the disaccharide β-D-Gal-(1 → 3)-α-D-GalNAc. A new procedure for synthesizing AFGPs using Fmoc-(Ac4-β-D-Gal-(1 → 3)-benzylidene-α-D-GalNAc)Thr-OH (10) as a building block has been developed. Total synthesis of the AFGPs (n=4, 8) in overall yields of 61% and 33%, respectively, has demonstrated the usefulness of the method. The synthetic AFGPs 1 (n=4, 8) showed a similar conformation to the native AFGPs in their circular dichroism spectra.

AB - The antifreeze glycoproteins (AFGPs) 1 are composed of a repeating tripeptide unit (Ala-Thr-Ala) in which the threonine residue is glycosylated with the disaccharide β-D-Gal-(1 → 3)-α-D-GalNAc. A new procedure for synthesizing AFGPs using Fmoc-(Ac4-β-D-Gal-(1 → 3)-benzylidene-α-D-GalNAc)Thr-OH (10) as a building block has been developed. Total synthesis of the AFGPs (n=4, 8) in overall yields of 61% and 33%, respectively, has demonstrated the usefulness of the method. The synthetic AFGPs 1 (n=4, 8) showed a similar conformation to the native AFGPs in their circular dichroism spectra.

KW - Antifreeze

KW - Glycoproteins

KW - Peptides

KW - Solid-phase synthesis

KW - T antigen

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Facile solid-phase synthesis of an antifreeze glycoprotein

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Keywords

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