Beilstein J. Org. Chem.2019,15, 1581–1591, doi:10.3762/bjoc.15.162
each hydroxy group in the threonine side chain is glycosylated with the disaccharide β-ᴅ-galactosyl-(1→3)-α-N-acetyl-ᴅ-galactosamine [4].
Even though the macroscopic properties of AFGPs, such as thermal hysteresis [5][6] and icerecrystallization inhibition [7][8][9] have been well described, the
analogues, which occasionally occurs in smaller natural AFGP (and furthermore proline is a precursor of the PP II helix) significantly decreased the inhibitory effect on the icerecrystallization of the compounds [19].
Here we present the synthesis of a series of model peptides comprising structural motifs
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Graphical Abstract
Figure 1:
Glycosylated building blocks prepared for solid phase peptide synthesis (SPPS).
Beilstein J. Org. Chem.2012,8, 1657–1667, doi:10.3762/bjoc.8.190
replacement of L-threonine by its allo-L-diastereomer. Both glycopeptides were analyzed regarding their conformational properties, by circular dichroism (CD), and their ability to inhibit icerecrystallization in microphysical experiments.
Keywords: bioorganic chemistry; circular dichroism; glycopeptides
; icerecrystallization; microwave chemistry; Introduction
Several fish species living in polar and subpolar oceans have developed a strategy to survive in water at an average temperature of −1.8 °C. This non-colligative freezing-point depression is based on the prevention of ice growth in
and the retro-inverso analogue 7 were tested in this study in an ice-recrystallization-inhibition assay [34][35][36][37]. In the absence of any active additives a polycrystalline ice sample undergoes Ostwald ripening at constant temperatures driven by the reduction of the total ice/solution interface
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Graphical Abstract
Scheme 1:
Synthesis of the monosaccharide-substituted threonine building block (A = allo-L-threonine; B = D-t...