کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
10592754 | 981798 | 2014 | 5 صفحه PDF | دانلود رایگان |
عنوان انگلیسی مقاله ISI
A tetradecapeptide somatostatin dicarba-analog: Synthesis, structural impact and biological activity
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کلمات کلیدی
موضوعات مرتبط
مهندسی و علوم پایه
شیمی
شیمی آلی
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چکیده انگلیسی
We described here the first tetradecapeptide somatostatin-analogue where the disulfide bridge has been replaced by a carbon-carbon double bond. This analogue was prepared using microwave assisted ring closing metathesis (RCM) using the 2nd generation Grubbs as catalyst. Under our optimized conditions the cyclization between allylGly 3 and 14 proceeded in moderate yield, excellent cyclic/linear ratio and very high Z-double bond selectivity. NMR studies also demonstrated that the conformational flexibility of this peptide is increased in comparison to that of the natural hormone. Remarkably, this alkene-bridged somatostatin analog is highly selective against somatostatin receptors 1 and 5, suggesting that conformational rigidity is not required for the efficient interaction of somatostatin analogues with these two receptors.
ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Bioorganic & Medicinal Chemistry Letters - Volume 24, Issue 1, 1 January 2014, Pages 103-107
Journal: Bioorganic & Medicinal Chemistry Letters - Volume 24, Issue 1, 1 January 2014, Pages 103-107
نویسندگان
Pablo MartÃn-Gago, Rosario Ramón, Eric Aragón, Jimena Fernández-Carneado, Pau Martin-Malpartida, Xavier Verdaguer, Pilar López-Ruiz, Begoña Colás, MarÃa Alicia Cortes, Berta Ponsati, Maria J. Macias, Antoni Riera,