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β NO Turns and Helices Induced by β 2 ‐Aminoxy Peptides: Synthesis and Conformational Studies
Author(s) -
Jiao ZhiGang,
Chang XiaoWei,
Ding Wei,
Liu GuoJun,
Song KeSheng,
Zhu NianYong,
Zhang DanWei,
Yang Dan
Publication year - 2011
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201000933
Subject(s) - intramolecular force , monomer , chemistry , hydrogen bond , crystallography , stereochemistry , solid state , ring (chemistry) , molecule , polymer , organic chemistry
Herein, we report an efficient route for the asymmetric synthesis of β 2 ‐aminoxy acids as well as experimental and theoretical studies of conformations of peptides composed of β 2 ‐aminoxy acids. The nine‐membered‐ring intramolecular hydrogen bonds, namely, β NO turns, are generated between adjacent residues in those peptides, in accordance with our computational results. The presence of two consecutive homochiral β NO turns leads to the formation of β NO helical structures in solution, although both helical (composed of two β NO turns of the same handedness) and reverse‐turn (composed of two β NO turns with opposite handedness) structures are of similar stability, as suggested by theoretical studies. Nevertheless, two slightly different conformations, with the same handedness, of β 2 ‐aminoxy monomers have been observed in the solid state and in solution according to our X‐ray and 2D NOESY studies.