Parallel synthesis of cyclic sugar amino acid/amino acid hybrid molecules

被引:64
作者
van Well, RM [1 ]
Overkleeft, HS [1 ]
Overhand, M [1 ]
Carstenen, EV [1 ]
van der Marel, GA [1 ]
van Boom, JH [1 ]
机构
[1] Leiden Univ, Gorlaeus Labs, Leiden Inst Chem, NL-2300 RA Leiden, Netherlands
关键词
sugar amino acid; host molecule; robot-assisted SPS; oxime linker;
D O I
10.1016/S0040-4039(00)01693-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of a furanoid sugar amino acid and its application in a parallel robot-assisted construction of cyclic sugar amino acid/amino acid hybrids as new potential host molecules is described. A cursory structural analysis by NMR revealed that one of the resulting cyclic hybrids (i.e. 2b) adopts a preferred conformation. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:9331 / 9335
页数:5
相关论文
共 25 条
[1]   COUPLED CYCLODEXTRIN APPENDING IMIDAZOLE AS AN ENZYME MODEL [J].
AKIIKE, T ;
NAGANO, Y ;
YAMAMOTO, Y ;
NAKAMURA, A ;
IKEDA, H ;
UENO, A ;
TODA, F .
CHEMISTRY LETTERS, 1994, (06) :1089-1092
[2]   Amino acid derivatives of beta-cyclodextrin [J].
Ashton, PR ;
Koniger, R ;
Stoddart, JF ;
Alker, D ;
Harding, VD .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (03) :903-908
[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]  
DEDJAINIPILARD F, 1993, TETRAHEDRON LETT, V34, P2457
[5]   Fluorescent cyclodextrins for molecule sensing: Fluorescent properties, NMR characterization, and inclusion phenomena of N-dansylleucine-modified cyclodextrins [J].
Ikeda, H ;
Nakamura, M ;
Ise, N ;
Oguma, N ;
Nakamura, A ;
Ikeda, T ;
Toda, F ;
Ueno, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (45) :10980-10988
[6]   MOLECULAR RECOGNITION OF CARBOHYDRATES USING A SYNTHETIC RECEPTOR - A MODEL SYSTEM TO UNDERSTAND THE STEREOSELECTIVITY OF A CARBOHYDRATE-CARBOHYDRATE INTERACTION IN WATER [J].
JIMENEZBARBERO, J ;
JUNQUERA, E ;
MARTINPASTOR, M ;
SHARMA, S ;
VICENT, C ;
PENADES, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (45) :11198-11204
[7]   Methods for selective modifications of cyclodextrins [J].
Khan, AR ;
Forgo, P ;
Stine, KJ ;
D'Souza, VT .
CHEMICAL REVIEWS, 1998, 98 (05) :1977-1996
[8]  
KUIJPERS WH, 1997, ISLAR 97 P, P107
[9]  
Lohof E, 2000, ANGEW CHEM INT EDIT, V39, P2761, DOI 10.1002/1521-3773(20000804)39:15<2761::AID-ANIE2761>3.0.CO
[10]  
2-9