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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ftunivottawa:oai:ruor.uottawa.ca:10393/28186 2023-05-15T13:37:48+02:00 Synthesis of a C-linked antifreeze glycoprotein building block containing an internal olefin Rana, Tahir 2009 179 p. application/pdf http://hdl.handle.net/10393/28186 https://doi.org/10.20381/ruor-12431 en eng University of Ottawa (Canada) Source: Masters Abstracts International, Volume: 48-05, page: 3010. http://hdl.handle.net/10393/28186 http://dx.doi.org/10.20381/ruor-12431 Chemistry Biochemistry Thesis 2009 ftunivottawa https://doi.org/10.20381/ruor-12431 2021-01-04T17:09:22Z 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 uO Research (University of Ottawa - uOttawa) Antarctic |
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Open Polar |
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uO Research (University of Ottawa - uOttawa) |
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ftunivottawa |
language |
English |
topic |
Chemistry Biochemistry |
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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 |
University of Ottawa (Canada) |
publishDate |
2009 |
url |
http://hdl.handle.net/10393/28186 https://doi.org/10.20381/ruor-12431 |
geographic |
Antarctic |
geographic_facet |
Antarctic |
genre |
Antarc* Antarctic |
genre_facet |
Antarc* Antarctic |
op_relation |
Source: Masters Abstracts International, Volume: 48-05, page: 3010. http://hdl.handle.net/10393/28186 http://dx.doi.org/10.20381/ruor-12431 |
op_doi |
https://doi.org/10.20381/ruor-12431 |
_version_ |
1766097963572002816 |