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| Title: | Synthesis of [l-Isoleucine-, 3-Proline-, and 5-Alanine ]-angiotensins 11 |
| Authors: | Khosla, M C Chaturvedi, N C Smeby, R R Bumpus, F M |
| Keywords: | 1-Isoleucine dicyclohexylcarbodiimide N-ethyl-5-phenylisoxazolium-3-sulfonate angiotensin |
| Issue Date: | 1968 |
| Citation: | Biochemistry, 7,1968,3417 |
| Abstract: | 1-Isoleucine,5-isoleucine]-angiotensin II and
[3-proline,5-isoleucine]-angiotensin II were synthesized by the solid-phase method using dicyclohexylcarbodiimide as the condensing agent. The formation of the arginyl-proline bond was extremely difficult under conditions
used. The former had about 25% pressor and
50% oxytocic activities giving further evidence the acidity of the j3-carboxyl is unnecessary. The latter possessed 40% pressor and 80% oxytocic activities of
the parent angiotensin. This relatively high biological activity was surprising because of the limitation on possible peptide conformations imposed by this cyclic
amino acid. [5-Alanine]-angiotensin II was prepared by solid phase using N-ethyl-5-phenylisoxazolium-3-sulfonate as the condensing agent. This peptide possessed
approximately 5% of pressor activity of angiotensin II indicating the importance of branched side chain of valine or isoleucine occurring naturally in this position. |
| URI: | http://hdl.handle.net/123456789/557 |
| Appears in Collections: | Medicinal and Process Chemistry
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| American Chem. Society-7-1968-3417.pdf | | 3927Kb | Adobe PDF | View/Open |
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