TY - JOUR
T1 - Design and synthesis of antifreeze glycoproteins and mimics
AU - Garner, James
AU - Harding, Margaret M.
PY - 2010/12/10
Y1 - 2010/12/10
N2 - Antifreeze glycoproteins are an important class of biological antifreezes that have potential applications in many areas of medicine, agriculture and industry in which ice crystal growth is damaging. While the synthesis of antifreeze glycoproteins as pure glycoforms has recently been achieved by using ligation and polymerisation strategies, the routine production of large quantities of pure glycoforms remains challenging. A range of C-linked analogues that are readily produced by solid-phase synthesis have delivered novel compounds that are not biological antifreezes, but are potent, non-cytotoxic, ice-recrystallisation inhibitors. Structure-activity studies, the identification of cyclic antifreeze glycoproteins and conformational studies have provided further insight into the requirements for antifreeze activity. These results, coupled with significant advances in approaches to the routine synthesis of different glycoproteins and mimics, present opportunities for the design and synthesis of novel ice-growth-inhibiting and antifreeze compounds. On ice: New synthetic routes to antifreeze glycoproteins as pure glycoforms, the identification of cyclic antifreeze glycoproteins, structure-activity studies, conformational studies and the properties of novel C-linked analogues, present opportunities for the design and synthesis of novel ice-growth-inhibiting and antifreeze compounds.
AB - Antifreeze glycoproteins are an important class of biological antifreezes that have potential applications in many areas of medicine, agriculture and industry in which ice crystal growth is damaging. While the synthesis of antifreeze glycoproteins as pure glycoforms has recently been achieved by using ligation and polymerisation strategies, the routine production of large quantities of pure glycoforms remains challenging. A range of C-linked analogues that are readily produced by solid-phase synthesis have delivered novel compounds that are not biological antifreezes, but are potent, non-cytotoxic, ice-recrystallisation inhibitors. Structure-activity studies, the identification of cyclic antifreeze glycoproteins and conformational studies have provided further insight into the requirements for antifreeze activity. These results, coupled with significant advances in approaches to the routine synthesis of different glycoproteins and mimics, present opportunities for the design and synthesis of novel ice-growth-inhibiting and antifreeze compounds. On ice: New synthetic routes to antifreeze glycoproteins as pure glycoforms, the identification of cyclic antifreeze glycoproteins, structure-activity studies, conformational studies and the properties of novel C-linked analogues, present opportunities for the design and synthesis of novel ice-growth-inhibiting and antifreeze compounds.
KW - Antifreeze
KW - Glycoproteins
KW - Glycosylation
KW - Peptide mimics
KW - Synthesis design
UR - http://www.scopus.com/inward/record.url?scp=78650013506&partnerID=8YFLogxK
U2 - 10.1002/cbic.201000509
DO - 10.1002/cbic.201000509
M3 - Review article
SN - 1439-4227
VL - 11
SP - 2489
EP - 2498
JO - ChemBioChem
JF - ChemBioChem
IS - 18
ER -