Synthesis of a C-linked antifreeze glycoprotein building block containing an internal olefin
Antifreeze glycoproteins (AFGPs) are polypeptide compounds found in the blood of Antarctic notothenioids and northern cod. These substances inhibit the growth and proliferation of ice in fish inhabiting sub-zero conditions. The structure of AFGPs, and the mechanism of ice growth inhibition at the mo...
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Université d'Ottawa / University of Ottawa
2009
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ftdatacite:10.20381/ruor-12431 2023-05-15T13:32:37+02:00 Synthesis of a C-linked antifreeze glycoprotein building block containing an internal olefin Rana, Tahir 2009 https://dx.doi.org/10.20381/ruor-12431 http://www.ruor.uottawa.ca/handle/10393/28186 en eng Université d'Ottawa / University of Ottawa Chemistry, Biochemistry. Text Thesis article-journal ScholarlyArticle 2009 ftdatacite https://doi.org/10.20381/ruor-12431 2021-11-05T12:55:41Z Antifreeze glycoproteins (AFGPs) are polypeptide compounds found in the blood of Antarctic notothenioids and northern cod. These substances inhibit the growth and proliferation of ice in fish inhabiting sub-zero conditions. The structure of AFGPs, and the mechanism of ice growth inhibition at the molecular level have been a source of intense debate. Work in our laboratory involves the synthesis of AFGP analogues in an effort to discern the mechanism of ice growth inhibition and enhance antifreeze attributes for potential therapeutic applications. We have previously synthesized C-linked AFGP analogues possessing antifreeze properties (TH, RI and DIS). One such analogue, [OGG] 4[Gal], has exhibited recrystallization inhibition (RI) activity comparable to native AFGPs. An important structural feature of [OGG]4[Gal] is the presence of an amide bond. We report herein the synthesis of a C-linked AFGP building block with an internal olefin as an amide isostere, in an effort to elucidate the function of the amide bond in the recrystallization inhibition activity of [OGG]4[Gal]. Thesis Antarc* Antarctic DataCite Metadata Store (German National Library of Science and Technology) Antarctic |
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Open Polar |
collection |
DataCite Metadata Store (German National Library of Science and Technology) |
op_collection_id |
ftdatacite |
language |
English |
topic |
Chemistry, Biochemistry. |
spellingShingle |
Chemistry, Biochemistry. Rana, Tahir Synthesis of a C-linked antifreeze glycoprotein building block containing an internal olefin |
topic_facet |
Chemistry, Biochemistry. |
description |
Antifreeze glycoproteins (AFGPs) are polypeptide compounds found in the blood of Antarctic notothenioids and northern cod. These substances inhibit the growth and proliferation of ice in fish inhabiting sub-zero conditions. The structure of AFGPs, and the mechanism of ice growth inhibition at the molecular level have been a source of intense debate. Work in our laboratory involves the synthesis of AFGP analogues in an effort to discern the mechanism of ice growth inhibition and enhance antifreeze attributes for potential therapeutic applications. We have previously synthesized C-linked AFGP analogues possessing antifreeze properties (TH, RI and DIS). One such analogue, [OGG] 4[Gal], has exhibited recrystallization inhibition (RI) activity comparable to native AFGPs. An important structural feature of [OGG]4[Gal] is the presence of an amide bond. We report herein the synthesis of a C-linked AFGP building block with an internal olefin as an amide isostere, in an effort to elucidate the function of the amide bond in the recrystallization inhibition activity of [OGG]4[Gal]. |
format |
Thesis |
author |
Rana, Tahir |
author_facet |
Rana, Tahir |
author_sort |
Rana, Tahir |
title |
Synthesis of a C-linked antifreeze glycoprotein building block containing an internal olefin |
title_short |
Synthesis of a C-linked antifreeze glycoprotein building block containing an internal olefin |
title_full |
Synthesis of a C-linked antifreeze glycoprotein building block containing an internal olefin |
title_fullStr |
Synthesis of a C-linked antifreeze glycoprotein building block containing an internal olefin |
title_full_unstemmed |
Synthesis of a C-linked antifreeze glycoprotein building block containing an internal olefin |
title_sort |
synthesis of a c-linked antifreeze glycoprotein building block containing an internal olefin |
publisher |
Université d'Ottawa / University of Ottawa |
publishDate |
2009 |
url |
https://dx.doi.org/10.20381/ruor-12431 http://www.ruor.uottawa.ca/handle/10393/28186 |
geographic |
Antarctic |
geographic_facet |
Antarctic |
genre |
Antarc* Antarctic |
genre_facet |
Antarc* Antarctic |
op_doi |
https://doi.org/10.20381/ruor-12431 |
_version_ |
1766028700523954176 |