Building addressable libraries: Site-selective formation of an N-acyliminium ion intermediate

被引：20

作者：

Kesselring, David ^{[1
]}

Maurer, Karl ^{[2
]}

Moeller, Kevin D. ^{[1
]}

机构：

[1] Washington Univ, Dept Chem, St Louis, MO 63130 USA

[2] CombiMatrix Corp, Mukilteo, WA 98275 USA

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 12期

关键词：

D O I：

10.1021/ol8007827

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A strategy for site-selectively generating reactive N-acyliminium ion intermediates on a microelectrode array has been developed. The route capitalizes on the use of an electroauxiliary for building a methoxylated amino acid substrate, and then the electrochemical generation and solution phase confinement of acid in order to form the N-acyliminium ion. Keys to this strategy were the stability of an N-alpha-methoxyalkyl amide to basic reaction conditions and the generality of the electrogenerated acid conditions for conducting microelectrode array reactions in a site-selective fashion.

引用

页码：2501 / 2504

页数：4

共 46 条

[1]

Aube J, 1997, ADV AMIN AC MIM PEPT, V1, P193

[2] Anodic amide oxidation/olefin metathesis strategies: Developing a unified approach to the synthesis of bicyclic lactam peptidomimetics [J].

Beal, LM ;

Liu, B ;

Chu, WH ;

Moeller, KD .

TETRAHEDRON, 2000, 56 (52) :10113-10125

[3] Design, synthesis, and application of azabicyclo[XYO]alkanone amino acids as constrained dipeptide surrogates and peptide mimics [J].

Cluzeau, J ;

Lubell, WD .

BIOPOLYMERS, 2005, 80 (2-3) :98-150

[4] Synthesis of new bicyclic lactam peptidomimetics by ring-closing metathesis reactions [J].

Colombo, L ;

Di Giacomo, M ;

Vinci, V ;

Colombo, M ;

Manzoni, L ;

Scolastico, C .

TETRAHEDRON, 2003, 59 (25) :4501-4513

[5] ANODIC AMIDE OXIDATIONS - CONFORMATIONALLY RESTRICTED PEPTIDE BUILDING-BLOCKS FROM THE DIRECT OXIDATIONS OF DIPEPTIDES [J].

CORNILLE, F ;

FOBIAN, YM ;

SLOMCZYNSKA, U ;

BEUSEN, DD ;

MARSHALL, GR ;

MOELLER, KD .

TETRAHEDRON LETTERS, 1994, 35 (38) :6989-6992

[6] ELECTROCHEMICAL CYCLIZATION OF DIPEPTIDES TOWARD NOVEL BICYCLIC, REVERSE-TURN PEPTIDOMIMETICS .1. SYNTHESIS AND CONFORMATIONAL-ANALYSIS OF 7,5-BICYCLIC SYSTEMS [J].

CORNILLE, F ;

SLOMCZYNSKA, U ;

SMYTHE, ML ;

BEUSEN, DD ;

MOELLER, KD ;

MARSHALL, GR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (03) :909-917

[7] A short synthesis of bicyclic dipeptides corresponding to Xxx-L-pro Xxx-D-pro having constrained trans-proline amides [J].

Curran, TP ;

Marcaurelle, LA ;

O'Sullivan, KM .

ORGANIC LETTERS, 1999, 1 (08) :1225-1228

[8] Antigen detection using microelectrode array microchips [J].

Dill, K ;

Montgomery, DD ;

Wang, W ;

Tsai, JC .

ANALYTICA CHIMICA ACTA, 2001, 444 (01) :69-78

[9] Synthesis and dopamine receptor modulating activity of 3-substituted γ-lactam peptidomimetics of L-prolyl-L-leucyl-glycinamide [J].

Dolbeare, K ;

Pontoriero, GF ;

Gupta, SK ;

Mishra, RK ;

Johnson, RL .

JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (05) :727-733

[10] Building constrained peptidomimetics: a convenient approach to 3-phenyl-5-vinyl substituted proline derivatives [J].

Duan, SQ ;

Moeller, KD .

TETRAHEDRON, 2001, 57 (30) :6407-6415

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