Combinatorial synthesis of amino acid- and peptide-carbohydrate conjugates on solid phase

被引：20

作者：

Opatz, T ^{[1
]}

Kallus, C ^{[1
]}

Wunberg, T ^{[1
]}

Kunz, H ^{[1
]}

机构：

[1] Johannes Gutenberg Univ Mainz, Inst Organ Chem, D-55128 Mainz, Germany

来源：

TETRAHEDRON | 2004年 / 60卷 / 39期

关键词：

combinatorial chemistry; solid-phase synthesis; carbohydrates; peptidomimetics; scaffolds;

D O I：

10.1016/j.tet.2004.05.101

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Carbohydrates are useful polyfunctional scaffold molecules which allow the selective attachment of a number of different side chains. The combinatorial solid phase synthesis of diverse amino acid or peptide conjugates of a polyfunctional glucose scaffold based on a set of selectively removable and orthogonally stable protecting groups is described. The resulting carbohydrate-peptide hybrids constitute potential turn mimetics. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：8613 / 8626

页数：14

共 38 条

[1] INTER-PROTON COUPLING OVER 5 BONDS 5J(H-C ALPHA-C(O)-N-C ALPHA-H) IN THE PEPTIDE MOIETY - THE IMPORTANCE OF SPECIFIC ASSOCIATION EFFECTS [J].

BARFIELD, M ;

ALOBEIDI, FA ;

HRUBY, VJ ;

WALTER, SR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (12) :3302-3306

[2] AN EFFICIENT METHOD FOR ANCHORING FMOC-AMINO ACIDS TO HYDROXYL-FUNCTIONALIZED SOLID SUPPORTS [J].

BLANKEMEYERMENGE, B ;

NIMTZ, M ;

FRANK, R .

TETRAHEDRON LETTERS, 1990, 31 (12) :1701-1704

[3] Folded conformation in peptides containing furanoid sugar amino acids [J].

Chakraborty, TK ;

Jayaprakash, S ;

Diwan, PV ;

Nagaraj, R ;

Jampani, SRB ;

Kunwar, AC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (49) :12962-12963

[4] Design, synthesis, and evaluation of the multidrug resistance reversing activity of D-glucose mimetics of hapalosin [J].

Dinh, TQ ;

Smith, CD ;

Du, XH ;

Armstrong, RW .

JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (06) :981-987

[5] SOLUTION SYNTHESIS OF A DIMERIC PENTAPEPTIDE - DIKETOPIPERAZINE CYCLIZATION OF GLU-ASP DIPEPTIDE ESTERS AND ASP-RACEMIZATION DURING SEGMENT CONDENSATION [J].

FISCHER, PM ;

SOLBAKKEN, M ;

UNDHEIM, K .

TETRAHEDRON, 1994, 50 (07) :2277-2288

[6] CARBOXYL-CATALYZED INTRAMOLECULAR AMINOLYSIS - SIDE REACTION IN SOLID-PHASE PEPTIDE SYNTHESIS [J].

GISIN, BF ;

MERRIFIELD, RB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (09) :3102-+

[7]

HarthFritschy E, 1997, J PEPT RES, V50, P415

[8] Modulation of receptor and receptor subtype affinities using diastereomeric and enantiomeric monosaccharide scaffolds as a means to structural and biological diversity. A new route to ether synthesis [J].

Hirschmann, R ;

Hynes, J ;

Cichy-Knight, MA ;

van Rijn, RD ;

Sprengeler, PA ;

Spoors, PG ;

Shakespeare, WC ;

Pietranico-Cole, S ;

Barbosa, J ;

Liu, J ;

Yao, WQ ;

Rohrer, S ;

Smith, AB .

JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (09) :1382-1391

[9] DE-NOVO DESIGN AND SYNTHESIS OF SOMATOSTATIN NONPEPTIDE PEPTIDOMIMETICS UTILIZING BETA-D-GLUCOSE AS A NOVEL SCAFFOLDING [J].

HIRSCHMANN, R ;

NICOLAOU, KC ;

PIETRANICO, S ;

LEAHY, EM ;

SALVINO, J ;

ARISON, B ;

CICHY, MA ;

SPOORS, PG ;

SHAKESPEARE, WC ;

SPRENGELER, PA ;

HAMLEY, P ;

SMITH, AB ;

REISINE, T ;

RAYNOR, K ;

MAECHLER, L ;

DONALDSON, C ;

VALE, W ;

FREIDINGER, RM ;

CASCIERI, MR ;

STRADER, CD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (26) :12550-12568

[10] NEW COUPLING REAGENTS IN PEPTIDE CHEMISTRY [J].

KNORR, R ;

TRZECIAK, A ;

BANNWARTH, W ;

GILLESSEN, D .

TETRAHEDRON LETTERS, 1989, 30 (15) :1927-1930

← 1 2 3 4 →