A reagent for the convenient, solid-phase synthesis of N-terminal peptide hydroxylamines for chemoselective ligations.
A reagent for the convenient, solid-phase synthesis of N-terminal peptide hydroxylamines for chemoselective ligations.
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DOI：
10.1021/ja900601c
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发表时间：
2009-03-25
影响因子：
15
通讯作者：
Bode JW
中科院分区：
文献类型：
--
作者：
Fukuzumi T;Bode JW
A newN-sulfonyloxaziridine reagent for the conversion of N-terminal peptide amines to the corresponding hydroxylamines without overoxidation or erosion of stereochemistry is described. The products are N-terminal hydroxylamines, which are substrates for chemoselective amide-bond forming reactions with α-ketoacids. The success of this reagent arises from covalent precomplexation with the substrate via imine bond formation followed by an intramolecular oxygen-atom transfer to the amine. An unexpected stereochemical mismatch between the racemic reagent and the chiral peptide substrates was addressed by the preparation of an enantipure version of this reagent and provides further support for the proposed mechanism.
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影响因子：
3.6
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Fields, JD;Kropp, PJ
通讯作者：
Kropp, PJ
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Vidal, J;Damestoy, S;Collet, A
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Collet, A
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作者：
Ju, Lei;Lippert, Alexander R.;Bode, Jeffrey W.
通讯作者：
Bode, Jeffrey W.
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LUSINCHI, X
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Tomkinson, Nicholas C. O.