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Oxytocin Analogues with O-Glycosylated Serine and Threonine in Position 4

Identyfikatory
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
Oxytocin structure was modified in position 4 using glycoamino acids. Procedure for transformation of Fmoc-protected serine and threonine derivatives into appropriate O-glycosylated precursors suitable for solid phase peptide synthesis (SPPS) was worked out. The alfa- and beta-O-glycosides were synthesized from Fmoc-serine and Fmoc-threonine allyl esters and appropriate glycosyl bromide using Hanessian's modification of the Koenigs-Knorr reaction. These N alfa-Fmoc-protected glycoamino acids were used in the synthesis of glycopeptides. Eight analogues of oxytocin were prepared. The obtained glycopeptides were tested for their rat uterotonic in vitro, pressor and antidiuretic activities and for their affinity to human oxytocin receptor. Moreover their stability towards alfa-chymotrypsin cleavage was studied.
Słowa kluczowe
Rocznik
Strony
1335--1344
Opis fizyczny
Bibliogr. 32 poz., rys.
Twórcy
autor
  • Department of Organic Chemistry, Faculty of Chemistry, University of Gdansk, Sobieskiego 18, 80-952 Gdansk, Poland, grzonka@chem.univ.gda.pl
Bibliografia
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Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUJ6-0014-0010
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