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Synthesis of [l-Isoleucine-, 3-Proline-, and 5-Alanine]-angiotensins.II

IR@CDRI: CSIR-Central Drug Research Institute, Lucknow

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Field Value
 
Creator Khosla, M C
Chaturvedi, N C
Smeby, R R
Bumpus, F M
 
Date 2010-08-23T10:27:05Z
2010-08-23T10:27:05Z
1968
 
Identifier Biochemistry,7,1968,3417-3421
http://hdl.handle.net/123456789/563
 
Description [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 ,a-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.
 
Format 3863937 bytes
application/pdf
 
Language en
 
Subject [1:-Isoleucine,5-isoleucine]-angiotensin II and
[5-Alanine]-angiotensin II
a-aspartyl-angiotensin
methylene group
 
Title Synthesis of [l-Isoleucine-, 3-Proline-, and 5-Alanine]-angiotensins.II
 
Type Article