N-Boc-Glutamic acid alpha-benzyl ester was transformed into 4-bromo-2-(tert-butoxycarbonylamino)-butyric acid benzyl ester using the Barton-Crich protocol. This bromo derivative undergoes nucleophilic substitution with nucleobases to give optically active N-Boc-4-adeninbutyrine (Boc-Aby), N-Boc-4-thyminbutyrine (Boc-Tby), N-Boc-4-guaninbutyrine (Boc-Gby) or N-Boc-4-cytosinbutyrine (Boc-Cby), useful building blocks for the synthesis of chiral peptidic nucleic acids (PNA).
Lenzi, A., Reginato, G., Taddei, M. (1995). Synthesis of N-boc-alpha-amino Acids With Nucleobase Residues As Building-blocks For the Preparation of Chiral Pna (peptidic Nucleic-acids). TETRAHEDRON LETTERS, 36(10), 1713-1716 [10.1016/0040-4039(95)00052-E].
Synthesis of N-boc-alpha-amino Acids With Nucleobase Residues As Building-blocks For the Preparation of Chiral Pna (peptidic Nucleic-acids)
Taddei, Maurizio
1995-01-01
Abstract
N-Boc-Glutamic acid alpha-benzyl ester was transformed into 4-bromo-2-(tert-butoxycarbonylamino)-butyric acid benzyl ester using the Barton-Crich protocol. This bromo derivative undergoes nucleophilic substitution with nucleobases to give optically active N-Boc-4-adeninbutyrine (Boc-Aby), N-Boc-4-thyminbutyrine (Boc-Tby), N-Boc-4-guaninbutyrine (Boc-Gby) or N-Boc-4-cytosinbutyrine (Boc-Cby), useful building blocks for the synthesis of chiral peptidic nucleic acids (PNA).
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https://hdl.handle.net/11365/31206
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