Synthesis and conformation of the cyclic octapeptides cyclo(Phe‐Pro) 4 , cyclo(Leu‐Pro) 4 , and cyclo[Lys(Z)‐Pro] 4 | Zendy

Kimura Shunsaku | Zendy; Imanishi Yukio | Zendy

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Synthesis and conformation of the cyclic octapeptides cyclo(Phe‐Pro) 4 , cyclo(Leu‐Pro) 4 , and cyclo[Lys(Z)‐Pro] 4

Author(s) -

Kimura Shunsaku,

Imanishi Yukio

Publication year - 1983

Publication title -

biopolymers

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.556

H-Index - 125

eISSN - 1097-0282

pISSN - 0006-3525

DOI - 10.1002/bip.360221006

Subject(s) - chemistry , cyclic peptide , stereochemistry , conformational isomerism , peptide , residue (chemistry) , isomerization , peptide bond , crystallography , molecule , organic chemistry , biochemistry , catalysis

Cyclic octapeptides, cyclo(X‐Pro) 4 , where X represents Phe, Leu, or Lys(Z), were synthesized and their conformations investigated. A C 2 ‐symmetric conformer containing two cis peptide bonds was found in all of these cyclic octapeptides. The numbers of available conformations due to the cis – trans isomerization of Pro peptide bonds depended on the nature of the solvent and X residue: they decreased in the following order: cyclo[Lys(Z)‐Pro] 4 > cyclo(Leu‐Pro) 4 > cyclo(Phe‐Pro) 4 in CDCl 3 . 13 C spin‐lattice relaxation times ( T 1 ) of these cyclic octapeptides were measured, and the contribution of segmental mobility to T 1 was found to vary with the nature of the X residue.

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