A simple method for the oxidation of α-amino acid esters to α-oximino esters

被引：3

作者：

Wu, Lisa Y. ^{[1
]}

Choi, Joseph K. ^{[1
]}

Hatton, Krit Y. ^{[1
]}

Berkman, Clifford E. ^{[1
]}

机构：

[1] Washington State Univ, Dept Chem, Pullman, WA 99164 USA

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 02期

关键词：

METABOLITE;

D O I：

10.1016/j.tetlet.2009.11.045

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Magnesium bis(monoperoxyphthalate) hexahydrate (MMPP) was found to be an effective reagent for the oxidation of various alpha-amino acid esters to the corresponding alpha-oximino acid esters. This transformation could be completed under mild conditions within 2.5 h using 1.1 equiv of MMPP in THF. Clean oximino esters were obtained after quenching and extracting the reaction from sodium thiosulfate solution. The O-phosphorylated derivative of 2-oximinoglutarate exhibited slow binding inhibitory potency for the metallopeptidase prostate-specific membrane antigen (PSMA) with an IC50 value of 58 nM. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：402 / 403

页数：2

共 9 条

[1] PHOSPHORUS(V) ACID ESTERS OF OXIMES [J].

ALLEN, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (12) :3071-3073

[2] Approaches to the synthesis of some tyrosine-derived marine sponge metabolites: Synthesis of verongamine and purealidin N [J].

Boehlow, TR ;

Harburn, JJ ;

Spilling, CD .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (09) :3111-3118

[3]

Heaney H., 1993, ALDRICHIM ACTA, V26, P35

[4] A CONVENIENT SYNTHESIS OF A BROMOTYROSINE DERIVED METABOLITE, PSAMMAPLIN-A, FROM PSAMMAPLYSILLA SP [J].

HOSHINO, O ;

MURAKATA, M ;

YAMADA, K .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1992, 2 (12) :1561-1562

[5] Efficient total synthesis of bastadin 6, an anti-angiogenic brominated tyrosine-derived metabolite from marine sponge [J].

Kotoku, N ;

Tsujita, H ;

Hiramatsu, A ;

Mori, C ;

Koizumi, N ;

Kobayashi, M .

TETRAHEDRON, 2005, 61 (30) :7211-7218

[6] Probing for a hydrophobic a binding register in prostate-specific membrane antigen with phenylalkylphosphonamidates [J].

Maung, J ;

Mallari, JP ;

Girtsman, TA ;

Wu, LY ;

Rowley, JA ;

Santiago, NM ;

Brunelle, AN ;

Berkman, CE .

BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (18) :4969-4979

[7] Inhibition of glutamate carboxypeptidase II by phosphonamidothionate derivatives of glutamic acid [J].

Rodriguez, CE ;

Lu, HY ;

Martinez, AR ;

Hu, Y ;

Brunelle, A ;

Berkman, CE .

JOURNAL OF ENZYME INHIBITION, 2001, 16 (04) :359-365

[8] Aerobic oxidation of primary amines to oximes catalyzed by DPPH and WO3/Al2O3 [J].

Suzuki, Ken ;

Watanabe, Tomonari ;

Murahashi, Shun-Ichi .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (11) :2079-2081

[9] Mild and efficient Lewis acid-promoted detritylation in the synthesis of N-hydroxy amides:: A concise synthesis of (-)-cobactin T [J].

Yang, Shyh-Ming ;

Lagu, Bharat ;

Wilson, Lawrence J. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (21) :8123-8126

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