New pyrazole containing bicarboxylic α-amino acids:: mimics of the cis amide bond

被引:19
作者
De Luca, L [1 ]
Falorni, M [1 ]
Giacomelli, G [1 ]
Porcheddu, A [1 ]
机构
[1] Univ Sassari, Dipartimento Chim, I-07100 Sassari, Italy
关键词
amino acids; amino acid derivatives; cycloadditions; pyrazoles;
D O I
10.1016/S0040-4039(99)01847-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of novel optically active oc-amino acids, containing a pyrazole ring, which can be regarded as building blocks for peptidomimetics, have been prepared starting from readily available oc-amino acids. The synthetic strategy employed allows the regio- and stereoselective preparation of 1,3- or 1,5-substituted pyrazolyl rings. The pyrazole containing peptidomimetics can be considered as analogues of peptides with a cis amide bond. (C) 1999 Elsevier Science Ltd, All rights reserved.
引用
收藏
页码:8701 / 8704
页数:4
相关论文
共 23 条
[1]  
ACHIWA K, 1975, TETRAHEDRON LETT, P2701
[2]   Residue-based control of helix shape in beta-peptide oligomers [J].
Appella, DH ;
Christianson, LA ;
Klein, DA ;
Powell, DR ;
Huang, XL ;
Barchi, JJ ;
Gellman, SH .
NATURE, 1997, 387 (6631) :381-384
[3]   TRYPTOPHAN-CONTAINING 1,5-TETRAZOLE DIPEPTIDE ANALOGS - SYNTHESIS OF TRP-PSI[CN4]NLE AS A CIS AMIDE BOND SURROGATE [J].
BOTEJU, LW ;
HRUBY, VJ .
TETRAHEDRON LETTERS, 1993, 34 (11) :1757-1760
[4]  
FALORNI M, 1987, GAZZ CHIM ITAL, V117, P7
[5]   Synthesis of new oxazole-containing peptidomimetics [J].
Falorni, M ;
Dettori, G ;
Giacomelli, G .
TETRAHEDRON-ASYMMETRY, 1998, 9 (08) :1419-1426
[6]   OPTICALLY-ACTIVE 4-OXAPROLINE DERIVATIVES - NEW USEFUL CHIRAL SYNTHONS DERIVED FROM SERINE AND THREONINE [J].
FALORNI, M ;
CONTI, S ;
GIACOMELLI, G ;
COSSU, S ;
SOCCOLINI, F .
TETRAHEDRON-ASYMMETRY, 1995, 6 (01) :287-294
[7]   Synthesis of chiral pyrazoles and isoxazoles as constrained amino acids [J].
Falorni, M ;
Giacomelli, G ;
Spanedda, AM .
TETRAHEDRON-ASYMMETRY, 1998, 9 (17) :3039-3046
[8]   Synthesis of new α-amino-acids containing the isoxazole moiety [J].
Falorni, M ;
Giacomelli, G ;
Spanu, E .
TETRAHEDRON LETTERS, 1998, 39 (50) :9241-9244
[9]   Conformational studies of chiral vinylogous sulfonamidopeptides [J].
Gennari, C ;
Salom, B ;
Potenza, D ;
Longari, C ;
Fioravanzo, E ;
Carugo, O ;
Sardone, N .
CHEMISTRY-A EUROPEAN JOURNAL, 1996, 2 (06) :644-655
[10]   ASYMMETRIC ELECTROPHILIC AMINATION - SYNTHESIS OF ALPHA-AMINO AND ALPHA-HYDRAZINO ACIDS WITH HIGH OPTICAL PURITY [J].
GENNARI, C ;
COLOMBO, L ;
BERTOLINI, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (20) :6394-6395