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• W2315046961 abstract "C-Linked antifreeze glycoprotein (C-AFGP) analogues have been shown to have potent ice recrystallization inhibition (IRI) activity. However, the lengthy synthesis of these compounds is not amenable to large-scale preparation for the many commercial, industrial, and medical applications that exist. This paper describes the synthesis of triazole-containing AFGPs using a convergent solid-phase synthesis (SPS) approach in which multiple carbohydrate derivatives are coupled to a resin-bound synthetic peptide in a single step. Modified “Click” conditions using dry DMF as solvent with catalytic Cu(II), sodium ascorbate, and microwave radiation afforded the synthesis of AFGP analogues 9−12 in 16−54% isolated yield. Compound 9 demonstrated no IRI activity, while compounds 10, 11, and 12 were moderate inhibitors of ice recrystallization. These results suggest that, while the triazole group is a structural mimetic of an amide bond, the amide bond in C-AFGP analogue 3 is an essential structural feature necessary for potent IRI activity." @default.
• W2315046961 created "2016-06-24" @default.
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• W2315046961 date "2011-04-01" @default.
• W2315046961 modified "2023-09-28" @default.
• W2315046961 title "Synthesis of <i>C</i>-Linked Triazole-Containing AFGP Analogues and Their Ability to Inhibit Ice Recrystallization" @default.
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• W2315046961 doi "https://doi.org/10.1021/bc100394k" @default.
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• W2315046961 hasPublicationYear "2011" @default.
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