Total Synthesis of Homogeneous Antifreeze Glycopeptides and Glycoproteins

Brendan Wilkinson; Robin S Stone; Chantelle J Capicciotti; Morten Thaysen-Andersen; Jacqueline M Matthews; Nicolle H Packer; Robert N Ben; Richard J Payne

doi:10.1002/anie.201108682

Total Synthesis of Homogeneous Antifreeze Glycopeptides and Glycoproteins

Brendan Wilkinson, Robin S Stone, Chantelle J Capicciotti, Morten Thaysen-Andersen, Jacqueline M Matthews, Nicolle H Packer, Robert N Ben, Richard J Payne

Chemistry

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

114 Citations (Scopus)

Abstract

Antifreeze glycoproteins (AFGPs) are a class of natural products found in deep sea teleost fish in Arctic and Antarctic waters. The physiological role of these biomolecules is to protect against cryoinjury in environments with subzero temperatures by preventing the growth of ice crystals in vivo.[¹] Structurally, AFGPs are polymeric, mucin-type glycoproteins that consist of a single glycotripeptide repeat (Ala-Thr-Ala/Pro) in which each secondary hydroxy group on threonine is linked to the disaccharide b-d-galactosyl-(1→3)- a-N-acetyl-d-galactosamine (Scheme 1).[²]

Original language	English
Pages (from-to)	3606-3610
Journal	Angewandte Chemie (International Edition)
Volume	51
Issue number	15
DOIs	https://doi.org/10.1002/anie.201108682
Publication status	Published - 2012

Keywords

Biologically Active Molecules
Proteins and Peptides
Organic Chemical Synthesis

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https://hdl.handle.net/1959.11/20674

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title = "Total Synthesis of Homogeneous Antifreeze Glycopeptides and Glycoproteins",

abstract = "Antifreeze glycoproteins (AFGPs) are a class of natural products found in deep sea teleost fish in Arctic and Antarctic waters. The physiological role of these biomolecules is to protect against cryoinjury in environments with subzero temperatures by preventing the growth of ice crystals in vivo.[¹] Structurally, AFGPs are polymeric, mucin-type glycoproteins that consist of a single glycotripeptide repeat (Ala-Thr-Ala/Pro) in which each secondary hydroxy group on threonine is linked to the disaccharide b-d-galactosyl-(1→3)- a-N-acetyl-d-galactosamine (Scheme 1).[²]",

keywords = "Biologically Active Molecules, Proteins and Peptides, Organic Chemical Synthesis",

author = "Brendan Wilkinson and Stone, \{Robin S\} and Capicciotti, \{Chantelle J\} and Morten Thaysen-Andersen and Matthews, \{Jacqueline M\} and Packer, \{Nicolle H\} and Ben, \{Robert N\} and Payne, \{Richard J\}",

year = "2012",

doi = "10.1002/anie.201108682",

language = "English",

volume = "51",

pages = "3606--3610",

journal = "Angewandte Chemie (International Edition)",

issn = "1433-7851",

publisher = "Wiley-VCH Verlag GmbH \& Co KGaA",

number = "15",

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TY - JOUR

T1 - Total Synthesis of Homogeneous Antifreeze Glycopeptides and Glycoproteins

AU - Wilkinson, Brendan

AU - Stone, Robin S

AU - Capicciotti, Chantelle J

AU - Thaysen-Andersen, Morten

AU - Matthews, Jacqueline M

AU - Packer, Nicolle H

AU - Ben, Robert N

AU - Payne, Richard J

PY - 2012

Y1 - 2012

N2 - Antifreeze glycoproteins (AFGPs) are a class of natural products found in deep sea teleost fish in Arctic and Antarctic waters. The physiological role of these biomolecules is to protect against cryoinjury in environments with subzero temperatures by preventing the growth of ice crystals in vivo.[¹] Structurally, AFGPs are polymeric, mucin-type glycoproteins that consist of a single glycotripeptide repeat (Ala-Thr-Ala/Pro) in which each secondary hydroxy group on threonine is linked to the disaccharide b-d-galactosyl-(1→3)- a-N-acetyl-d-galactosamine (Scheme 1).[²]

AB - Antifreeze glycoproteins (AFGPs) are a class of natural products found in deep sea teleost fish in Arctic and Antarctic waters. The physiological role of these biomolecules is to protect against cryoinjury in environments with subzero temperatures by preventing the growth of ice crystals in vivo.[¹] Structurally, AFGPs are polymeric, mucin-type glycoproteins that consist of a single glycotripeptide repeat (Ala-Thr-Ala/Pro) in which each secondary hydroxy group on threonine is linked to the disaccharide b-d-galactosyl-(1→3)- a-N-acetyl-d-galactosamine (Scheme 1).[²]

KW - Biologically Active Molecules

KW - Proteins and Peptides

KW - Organic Chemical Synthesis

UR - https://www.scopus.com/pages/publications/84859540284

U2 - 10.1002/anie.201108682

DO - 10.1002/anie.201108682

M3 - Article

SN - 1433-7851

VL - 51

SP - 3606

EP - 3610

JO - Angewandte Chemie (International Edition)

JF - Angewandte Chemie (International Edition)

IS - 15

ER -

Total Synthesis of Homogeneous Antifreeze Glycopeptides and Glycoproteins

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