From capped to three-dimensional cyclodextrins:: the first example of a new class of receptors by trehalose capping of a β-cyclodextrin

被引:18
作者
Cucinotta, V
Grasso, G
Vecchio, G
机构
[1] Univ Naples Federico II, Dipartimento Sci Alimenti, I-80055 Napoli, Italy
[2] CNR, Ist Studio Sostanze Nat Interesse Alimentare & Ch, I-95125 Catania, Italy
[3] Univ Catania, Dipartimento Sci Chim, I-95125 Catania, Italy
关键词
cyclodextrins; capped cyclodextrins; inclusion; trehalose;
D O I
10.1023/A:1007994324973
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new capped derivative of cyclomaltoheptaose (CDTHCM) was synthesized by the reaction of 6,6'-dideoxy-6,6' -di(S-cysteamine)-alpha,alpha'-trehalose with 6A,6D-dideoxy-6A,6D-diiodo-cyclomaltoheptaose. The CDTHCM obtained was characterized, together with its behaviour towards protonation. The CDTHCM/ACS (anthraquinone-2-sulfonic acid sodium salt) system was investigated by (HNMR)-H-1 spectroscopy and by i.c.d. (induced circular dichroism) at two different pHs. The deep inclusion of ACS within the CDTHCM cavity, with an association constant about six times larger compared to the beta-CD/ACS system was found at pH 6.
引用
收藏
页码:43 / 55
页数:13
相关论文
共 20 条
[11]  
IKADA H, 1996, J AM CHEM SOC, V118, P10980
[12]  
KATO T, 1988, HETEROCYCLES, V27, P973
[13]   SYNTHETIC CARBOHYDRATE POLYMERS CONTAINING TREHALOSE RESIDUES IN THE MAIN-CHAIN - PREPARATION AND CHARACTERISTIC PROPERTIES [J].
KURITA, K ;
MASUDA, N ;
AIBE, S ;
MURAKAMI, K ;
ISHII, S ;
NISHIMURA, SI .
MACROMOLECULES, 1994, 27 (26) :7544-7549
[14]  
PERKAMPUS HH, 1992, UV VIS SPECTROSCOPY, P131
[15]   ARTIFICIAL RECEPTORS FOR AMINO-ACIDS IN WATER - LOCAL ENVIRONMENTAL-EFFECT ON POLAR RECOGNITION BY 6A-AMINO-6B-CARBOXY-CYCLODEXTRINS AND 6B-AMINO-6A-CARBOXY-BETA-CYCLODEXTRINS [J].
TABUSHI, I ;
KURODA, Y ;
MIZUTANI, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (15) :4514-4518
[16]  
TABUSHI I, 1976, J AM CHEM SOC, V98, P855
[17]  
Trotta F., 1996, J INCLUSION PHENOM, V23, P269
[18]   PHOTOCONTROL OF CATALYTIC ACTIVITY OF CAPPED CYCLODEXTRIN [J].
UENO, A ;
TAKAHASHI, K ;
OSA, T .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (03) :94-96
[19]   DIAZA-CROWN ETHER CAPPED CYCLODEXTRIN - A RECEPTOR WITH 2 RECOGNITION SITES [J].
WILLNER, I ;
GOREN, Z .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (24) :1469-1470
[20]  
YUAN DQ, 1996, J CHEM SOC CHEM COMM, P1943