Stereoselective synthesis of conformationally constrained reverse turn dipeptide mimetics

被引:84
作者
Qiu, W [1 ]
Gu, XY [1 ]
Soloshonok, VA [1 ]
Carducci, MD [1 ]
Hruby, VJ [1 ]
机构
[1] Univ Arizona, Dept Chem, Tucson, AZ 85721 USA
关键词
D O I
10.1016/S0040-4039(00)01864-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Peptide side chains play critical roles in the event of molecular recognition. In order to study the bioactive conformation of parent peptides, a concise and straightforward five-step synthesis of [5.5]-bicyclic reverse turn dipeptide mimetic scaffolds with side chain functionality at the i+1 and i+2 positions has been developed. In the bicyclic structure, two dihedral angles (psi (2) and phi (3)) are greatly restricted. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:145 / 148
页数:4
相关论文
共 24 条
[1]  
Al-Obeidi F, 1998, J PEPT RES, V51, P420
[2]   Solid-phase synthesis and structural analysis of bicyclic β-turn mimetics incorporating functionality at the i to i+3 positions [J].
Eguchi, M ;
Lee, MS ;
Nakanishi, H ;
Stasiak, M ;
Lovell, S ;
Kahn, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (51) :12204-12205
[3]   Design, synthesis, and conformational analysis of a proposed type I β-turn mimic [J].
Fink, BE ;
Kym, PR ;
Katzenellenbogen, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (18) :4334-4344
[4]   CONFORMATIONALLY CONSTRAINED NONPEPTIDE BETA-TURN MIMETICS OF ENKEPHALIN [J].
GARDNER, B ;
NAKANISHI, H ;
KAHN, M .
TETRAHEDRON, 1993, 49 (17) :3433-3448
[5]   New asymmetric syntheses of beta-hydroxy alpha-amino acids and analogues. Components of biologically active cyclopeptides [J].
Genet, JP .
PURE AND APPLIED CHEMISTRY, 1996, 68 (03) :593-596
[6]  
Gillespie P, 1997, BIOPOLYMERS, V43, P191, DOI 10.1002/(SICI)1097-0282(1997)43:3<191::AID-BIP2>3.3.CO
[7]  
2-2
[8]   Rigid dipeptide surrogates: Syntheses of enantiopure quinolizidinone and pyrroloazepinone amino acids from a common diaminodicarboxylate precursor [J].
Gosselin, F ;
Lubell, WD .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (07) :2163-2171
[9]   Design and synthesis of conformationally constrained amino acids as versatile scaffolds and peptide mimetics [J].
Hanessian, S ;
McNaughtonSmith, G ;
Lombart, HG ;
Lubell, WD .
TETRAHEDRON, 1997, 53 (38) :12789-12854
[10]   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