非タンパク質構成アミノ酸の設計・合成とそのペプチドの2次構造

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概要

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• Replacement of the α-hydrogen atom of L-α-amino acids with an alkyl substituent results in α, α-disubstituted amino acids. The modification changes the properties of the amino acids. Incorporation of α, α-disubstituted amino acids into oligopeptides restricts the conformational freedom of their peptides. The author developed a synthetic route for optically active α-ethylated α, α-disubstituted amino acids using chiral cyclic 1, 2-diol, and disclosed that the preferred conformation of peptides composed of chiral α-ethylated disubstituted amino acids is a fully planar conformation, whereas that of chiral α-methylated disubstituted amino acids is a 3_<10>-helical structure. Furthermore, the author designed and synthesized two chiral cyclic α, α-disubstituted amino acids, i.e., (3S, 4S) -1-amino-3, 4-di (methoxy) cyclopentanecarboxylic acid {(S, S) -Ac_5c^<dOM>}, and (1R, 6R) -8-aminobicyclo- [4. 3. 0] non-3-ene-8-carboxylic acid {(R, R) -Ab_<5, 6=>c}. They do not have a chiral center at the α-position, but do have chiral centers on the side-chain cyclopentane or the bicyclic skeleton. The preferred secondary structure of the (S, S) -Ac_5c^<dOM> homopeptides was the left-handed (M) 3_<10>-helical structure (hexapeptide) and the left-handed (M) α-helical structure (octa- and decapeptides), while that of the (R, R) -Ab_<5,6=>c hexapeptide was both the right-handed (P) and left-handed (M) 3_<10>-helices. These results indicate that the side-chain chiral centers affect the secondary structure of their peptides, and the side-chain chiral environment is important for the control of the helical-screw direction of peptides.

• 社団法人日本薬学会の論文
• 2006-10-01

著者

• 田中 正一

  Graduate School Of Pharmaceutical Sciences Kyushu University

• 田中 正一

  九州大学大学院薬学研究院

• Tanaka Muneo

  Research Center Shiseido Ltd.

• Tanaka M

  Faculty Of Pharmaceutical Sciences Tokushima Bunri University

• 田中 誠

  School Of Pharmaceutical Sciences Kitasato University

• Tanaka M

  Nihon Univ. Fujisawa‐shi Jpn

• Tanaka Masami

  Faculty Of Pharmaceutical Sciences Tokushima Bunri University

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