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Influence of L‐Leu to D‐Leu Replacement on the Helical Secondary Structures of L‐Leu‐Aib‐Based Dodecapeptides
Author(s) -
Demizu Yosuke,
Okitsu Koyo,
Doi Mitsunobu,
Misawa Takashi,
Oba Makoto,
Tanaka Masakazu,
Kurihara Masaaki
Publication year - 2016
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201601493
Subject(s) - protein secondary structure , molecule , peptide , residue (chemistry) , crystallography , stereochemistry , chemistry , organic chemistry , biochemistry
A dodecapeptide, Boc‐( L ‐Leu‐ L ‐Leu‐Aib‐ L ‐Leu‐ D ‐Leu‐Aib) 2 ‐OMe ( 2 ), was designed and synthesized to investigate the influence of L ‐Leu to D ‐Leu residue replacement on the helical secondary structure of L ‐Leu‐Aib‐based dodecapeptides. Its preferred conformation was analyzed based on its Fourier transform infrared spectra, CD spectra, and X‐ray diffraction. It was revealed that peptide 2 formed a mixture of right‐handed ( P ) 3 10 ‐ and α‐helical structures in solution, and eight helical molecules were assembled in the crystalline state.