L-gamma-Carboxyglutamic acid (Gla) is an uncommon amino acid that binds avidly to mineral surfaces and metal ions. Herein, we report the synthesis of N-alpha-Fmoc-L-gamma-carboxyglutamic acid gamma,gamma'-tert-butyl ester (Fmoc-Gla(O(t)Bu)(2)-OH), a suitably protected analogue for Fmoc-based solid-phase peptide synthesis. The residue was synthesized using a novel chiral Cu(II) complex, whose structure-based design was inspired by the blue copper protein rusticyanin. The five-coordinate complex is formed by Shiff base formation between glycine and the novel ligand (S)-2-(N-(2-methylthio)benzylproly)aminobenzophenone in the presence of copper. Michael addition of di-tert-butyl methylenemalonate to the alpha-carbon of the glycine portion of the complex occurs in a diastereoselective fashion. The resulting (S,S)-complex diastereomer can be easily purified by chromatography. Metal complex decomposition followed by Fmoc protection affords the enantiomerically pure amino acid. With the use of this novel chiral complex, the asymmetric synthesis of Fmoc-Gla(O(t)Bu)(2)-OH was completed in nine steps from thiosalicylic acid in 14.5% overall yield.
机构:S China Agr Univ, Coll Sci, Dept Appl Chem, Guangzhou 510642, Peoples R China
Liu, XP
Yang, C
论文数: 0引用数: 0
h-index: 0
机构:S China Agr Univ, Coll Sci, Dept Appl Chem, Guangzhou 510642, Peoples R China
Yang, C
Le, XY
论文数: 0引用数: 0
h-index: 0
机构:
S China Agr Univ, Coll Sci, Dept Appl Chem, Guangzhou 510642, Peoples R ChinaS China Agr Univ, Coll Sci, Dept Appl Chem, Guangzhou 510642, Peoples R China
Le, XY
Zhou, XH
论文数: 0引用数: 0
h-index: 0
机构:S China Agr Univ, Coll Sci, Dept Appl Chem, Guangzhou 510642, Peoples R China
Zhou, XH
Wu, LY
论文数: 0引用数: 0
h-index: 0
机构:S China Agr Univ, Coll Sci, Dept Appl Chem, Guangzhou 510642, Peoples R China
Wu, LY
Chen, S
论文数: 0引用数: 0
h-index: 0
机构:S China Agr Univ, Coll Sci, Dept Appl Chem, Guangzhou 510642, Peoples R China
机构:
S China Agr Univ, Coll Sci, Dept Appl Chem, Guangzhou 510642, Peoples R ChinaS China Agr Univ, Coll Sci, Dept Appl Chem, Guangzhou 510642, Peoples R China
Le, XY
Tong, ML
论文数: 0引用数: 0
h-index: 0
机构:S China Agr Univ, Coll Sci, Dept Appl Chem, Guangzhou 510642, Peoples R China
机构:
S China Agr Univ, Coll Sci, Dept Appl Chem, Guangzhou 510642, Peoples R ChinaS China Agr Univ, Coll Sci, Dept Appl Chem, Guangzhou 510642, Peoples R China
Le, XY
Zhou, XH
论文数: 0引用数: 0
h-index: 0
机构:S China Agr Univ, Coll Sci, Dept Appl Chem, Guangzhou 510642, Peoples R China
Zhou, XH
Huang, CJ
论文数: 0引用数: 0
h-index: 0
机构:S China Agr Univ, Coll Sci, Dept Appl Chem, Guangzhou 510642, Peoples R China
Huang, CJ
Feng, XL
论文数: 0引用数: 0
h-index: 0
机构:S China Agr Univ, Coll Sci, Dept Appl Chem, Guangzhou 510642, Peoples R China
机构:
Hebei Normal Univ, Coll Chem & Mat Sci, Shijiazhuang 050016, Hebei, Peoples R ChinaHebei Normal Univ, Coll Chem & Mat Sci, Shijiazhuang 050016, Hebei, Peoples R China
He Rong
Song Huihua
论文数: 0引用数: 0
h-index: 0
机构:
Hebei Normal Univ, Coll Chem & Mat Sci, Shijiazhuang 050016, Hebei, Peoples R ChinaHebei Normal Univ, Coll Chem & Mat Sci, Shijiazhuang 050016, Hebei, Peoples R China
Song Huihua
Wu Lili
论文数: 0引用数: 0
h-index: 0
机构:
Hebei Normal Univ, Coll Chem & Mat Sci, Shijiazhuang 050016, Hebei, Peoples R ChinaHebei Normal Univ, Coll Chem & Mat Sci, Shijiazhuang 050016, Hebei, Peoples R China
Wu Lili
Wei Zhen
论文数: 0引用数: 0
h-index: 0
机构:
Hebei Normal Univ, Coll Chem & Mat Sci, Shijiazhuang 050016, Hebei, Peoples R ChinaHebei Normal Univ, Coll Chem & Mat Sci, Shijiazhuang 050016, Hebei, Peoples R China
Wei Zhen
Wang Tao
论文数: 0引用数: 0
h-index: 0
机构:
Hebei Univ Sci & Technol, Coll Sci, Shijiazhuang 050018, Hebei, Peoples R ChinaHebei Normal Univ, Coll Chem & Mat Sci, Shijiazhuang 050016, Hebei, Peoples R China