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Stepwise Synthesis of γ ‐Glutamic Acid 16‐Mer
Author(s) -
Sanda Fumio,
Fujiyama Taizo,
Endo Takeshi
Publication year - 2002
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/1521-3935(20020301)203:4<727::aid-macp727>3.0.co;2-s
Subject(s) - chemistry , dimer , trimer , circular dichroism , tetramer , glutamic acid , histone octamer , stereochemistry , chirality (physics) , nmr spectra database , hydrolysis , proton nmr , amino acid , organic chemistry , enzyme , spectral line , biochemistry , nambu–jona lasinio model , chiral symmetry breaking , physics , quantum mechanics , astronomy , nucleosome , histone , gene , quark
γ ‐Glutamic acid 16‐mer α ‐ethyl ester was synthesized in stepwise transesterification of the ethyl ester group into benzyl ester group, followed by hydrogenation afforded γ ‐glutamic acid 16‐mer with free carboxyl groups. Alkaline hydrolysis of γ ‐glutamic acid 16‐mer α ‐ethyl ester also afforded 16‐mer with free carboxyl groups. The two 16‐mers showed similar circular dichroism spectra. The structures and optical properties of γ ‐glutamic acid dimer, trimer, tetramer, octamer, and 16‐mer were elucidated by 1 H NMR, 13 C NMR, IR, circular dichroism spectra, and X‐ray. Specific rotation of the intermediates of 16‐mer increased as the number of the glutamate unit.