Solid phase synthesis and conformation of sequential glycosylated polytripeptide sequences related to antifreeze glycoproteins.

  title={Solid phase synthesis and conformation of sequential glycosylated polytripeptide sequences related to antifreeze glycoproteins.},
  author={Fernando Filira and Laura Biondi and Barbara Scolaro and Maria Teresa Foffani and Stefano Mammi and Evaristo Peggion and Raniero Rocchi},
  journal={International journal of biological macromolecules},
  volume={12 1},
Sequential glycopeptides [Thr(beta-D-galactose)-Ala-Ala]n, with n ranging from 2 to 7, as models of natural antifreeze glycoproteins were synthesized by the continuous flow, solid phase procedure. The conformational properties of these materials in solution were investigated by c.d. and 1H-n.m.r. spectroscopy. In aqueous solution the c.d. pattern is practically independent of chain length and is very similar to that of natural antifreeze glycoproteins. The results are interpreted in terms of… Expand
Solution conformation of C-linked antifreeze glycoprotein analogues and modulation of ice recrystallization.
This study explores how changes in the length of the amide-containing side chain between the carbohydrate moiety and the polypeptide backbone in C-linked AFGP analogues influences ice recrystallization inhibition (IRI) activity. Expand
Facile solid-phase synthesis of an antifreeze glycoprotein.
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[6] Solid-phase synthesis of O-glycopeptides
Publisher Summary To study the influence of carbohydrate variation on the properties of a peptide or a protein, it has become important to have access to several different glycoforms. This can beExpand
Antifreeze glycopeptides: from structure and activity studies to current approaches in chemical synthesis
The current state of knowledge regarding the structure and activity of AFGPs, as well as approaches to organic synthesis of these molecules with focus on the most recent developments are presented. Expand
Influence of glycosylation on the conformational preferences of folded oligopeptides
Abstract Synthesis, characterization, and conformational analysis by FT-IR absorption, 1H NMR and X-ray diffraction techniques are described for a series of side-chain O-glycosylated Thr peptides ofExpand
A serendipitous discovery of antifreeze protein-specific activity in C-linked antifreeze glycoprotein analogs
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Chapter 4 Chemical Synthesis of Glycopeptides
Publisher Summary This chapter discusses the chemical synthesis of glycopeptides. Glycoproteins are composed of a polypeptide backbone which is glycosylated with one or more carbohydrate chains. TheExpand
Synthesis and antifreeze activity of fish antifreeze glycoproteins and their analogues
Fishes from both Arctic and Antarctic waters produce antifreeze glycoproteins (AFGPs) that modify and inhibit the growth of ice crystals, allowing them to survive in extreme cold conditions. TheseExpand
'Antifreeze' glycoproteins from polar fish.
The recent successful synthesis of small AFGPs using solution methods and solid-phase chemistry provides the opportunity to perform key structure-activity studies that would clarify the important residues and functional groups required for activity. Expand


Conformation of the antifreeze glycoprotein of polar fish.
High-field proton and 13C NMR spectroscopy has been used to test and refine the recent proposal of a threefold left-handed helical conformation for antifreeze glycoprotein (AFGP), indicating that AFGP fraction 8 is an extended "rod-like" conformation at low temperature which becomes a flexible coil at high temperature. Expand
Blood group antigens: synthesis of TN glycopeptide related to human glycophorin AM.
  • B. Ferrari, A. Pavia
  • Medicine, Chemistry
  • International journal of peptide and protein research
  • 1983
The above compound constitutes the G1-G5 sequence of the amino-terminal portion of human glycophorin AM, the main erythrocyte membrane glycoprotein, and was obtained by a stepwise peptide coupling strategy alternatively using aminoacids and adequately protected and/or activated O-glycosyl-aminoacids. Expand
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2,3,4,6-Tetra-O-acetyl-1-N-[N-(tert-butyloxycarbonyl)-L-aspart-4-oyl]-D-g lucopyranosylamine and 2-acetamido-3,4,6-tri-O-acetyl-1-N-[N-(tert-butyloxycarbonyl)-L-aspart-4-oyl]-2Expand
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The 1H NMR spectrum of the title peptide, H-Leu-(Glu)5-Ala-Tyr-Gly-Trp-Nle-Asp-Phe-NH2, in 90% H2O/10% D2O was assigned by two-dimensional methods, and the displacement of the proton resonances uponExpand
Synthesis of a glycotripeptide and a glycosomatostatin containing the 3-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-L-serine residue.
The structure of Gly-[beta-D-GlcpNAc-(1 leads to 3)-Ser]-Ala-OH was further confirmed by mass spectrometry of the N-acetyl permethyl derivative, and by n.m.r.c. spectroscopy. Expand
Natural abundance carbon 13 nuclear magnetic resonance spectroscopy of antifreeze glycoproteins.
Natural abundance 13C NMR spectroscopy (at 67.9 MHz) is used to study an aqueous solution of the antifreeze glycoproteins 3 to 6 from the Antarctic cod. Assignments of resonances to specific carbonsExpand