Novel and facile solution-phase synthesis of 2,5-diketopiperazines and O-glycosylated analogs

被引：16

作者：

Campo, Vanessa L. ^{[1
]}

Martins, Maristela B. ^{[1
]}

da Silva, Carlos H. T. P. ^{[1
]}

Carvalho, Ivone ^{[1
]}

机构：

[1] Univ Sao Paulo, Fac Ciencias Farmaceut Ribeirao Preto, BR-14040930 Ribeirao Preto, Brazil

来源：

TETRAHEDRON | 2009年 / 65卷 / 27期

基金：

巴西圣保罗研究基金会;

关键词：

Diketopiperazine; Dipeptide cyclization; Glycosylated amino acid; Solution-phase synthesis; COMBINATORIAL CHEMISTRY; BIOLOGICAL-ACTIVITY; BUILDING-BLOCKS; SMALL MOLECULES; AMINO ACIDS; DIKETOPIPERAZINES; ESTERS; DIMERIZATION; STRATEGY; PEPTIDE;

D O I：

10.1016/j.tet.2009.04.069

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This work describes the synthesis in Solution of a series of related diketopiperazines with potential biological activities: cyclo(L-Pro-L-Ser), cyclo(L-Phe-L-Ser), cyclo(D-Phe-L-Ser) and the corresponding glycosylated analogs of the latter, cyclo[D-Phe-L-Ser(alpha GlcNAc)] and cyclo[D-Phe-L-Ser(beta GlcNAc)]. The synthetic approach involved coupling reactions of -OH or O-glycosylated serine benzyl esters with NFmoc-protected amino acids (Pro or Phe), followed by one-pot deprotection-cyclization reaction in the presence of 20% piperidine in DMF. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：5343 / 5349

页数：7

共 25 条

[1] On the origins of diastereoselectivity in the alkylation of diketopiperazine enolates [J].

Bull, Steven D. ;

Davies, Stephen G. ;

Garner, A. Christopher ;

Parkes, Alastair L. ;

Roberts, Paul M. ;

Sellers, Thomas G. R. ;

Smith, Andrew D. ;

Tamayo, Juan A. ;

Thomson, James E. ;

Vickers, Richard J. .

NEW JOURNAL OF CHEMISTRY, 2007, 31 (04) :486-495

[2] Synthesis of glycosyl-amino acids of biological interest [J].

Campo, Vanessa Leiria ;

Carvalho, Ivone .

QUIMICA NOVA, 2008, 31 (05) :1027-1033

[3] Chemical and chemoenzymatic synthesis of glycosyl-amino acids and glycopeptides related to Trypanosoma cruzi mucins [J].

Campo, Vanessa Leiria ;

Carvalho, Ivone ;

Allman, Sarah ;

Davis, Benjamin G. ;

Field, Robert A. .

Organic and Biomolecular Chemistry, 2007, 5 (16) :2645-2657

[4] Practical synthesis of the 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucosides of Fmoc-serine and Fmoc-threonine and their benzyl esters [J].

Carvalho, I ;

Scheuerl, SL ;

Kartha, KPR ;

Field, RA .

CARBOHYDRATE RESEARCH, 2003, 338 (10) :1039-1043

[5] Diketopiperazines in peptide and combinatorial chemistry [J].

Fischer, PM .

JOURNAL OF PEPTIDE SCIENCE, 2003, 9 (01) :9-35

[6] Facile synthesis of orthogonally protected optically pure keto- and diketopiperazine building blocks for combinatorial chemistry [J].

Gellerman, G. ;

Hazan, E. ;

Brider, T. ;

Traube, T. ;

Albeck, A. ;

Shatzmiler, S. .

INTERNATIONAL JOURNAL OF PEPTIDE RESEARCH AND THERAPEUTICS, 2008, 14 (02) :183-192

[7] New general strategy of dimerization of bioactive molecules [J].

Giraud, M ;

Bernad, N ;

Martinez, J ;

Cavelier, F .

TETRAHEDRON LETTERS, 2001, 42 (10) :1895-1897

[8] Exploring privileged structures: The combinatorial synthesis of cyclic peptides [J].

Horton, DA ;

Bourne, GT ;

Smythe, ML .

MOLECULAR DIVERSITY, 2000, 5 (04) :289-304

[9] Unique diketopiperazine dimers from the insect pathogenic fungus Verticillium hemipterigenum BCC 1449 [J].

Isaka, M ;

Palasarn, S ;

Rachtawee, P ;

Vimuttipong, S ;

Kongsaeree, P .

ORGANIC LETTERS, 2005, 7 (11) :2257-2260

[10] Participation of aromatic side chains in diketopiperazine ensembles [J].

Joshi, K. B. ;

Verma, Sandeep .

TETRAHEDRON LETTERS, 2008, 49 (27) :4231-4234

← 1 2 3 →