Synthesis of amphiphilic chitoheptaose derivative

被引：5

作者：

Hinou, H

Umino, A

Matsuoka, K

Terunuma, D

Takahashi, S

Esumi, Y

Kuzuhara, H

机构：

[1] SAITAMA UNIV,FAC ENGN,DEPT FUNCT MAT SCI,URAWA,SAITAMA 338,JAPAN

[2] INST PHYS & CHEM RES,WAKO,SAITAMA 35101,JAPAN

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 46期

关键词：

D O I：

10.1016/S0040-4039(97)10104-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

With interest in clustering of bioactive chitooligosaccharides of more than dp 6, a chitoheptaose derivative 1 carrying tetradecanoyl and tetradecyloxy groups at the NH and the C-1 of the reducing end was prepared. The hydrophobic groups were introduced step by step after completion of the heptasaccharide skeleton using a chitobiose derivative as the elongation unit. Micelle formation of 1 in water was confirmed by dye solubilization check. (C) 1997 Elsevier Science Ltd.

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页码：8041 / 8044

页数：4

相关论文

共 11 条

[1]

FRASERREID B, 1992, SYNLETT, P927

[2] A NOVEL, REDUCTIVE RING-OPENING OF CARBOHYDRATE BENZYLIDENE ACETALS, WITH UNUSUAL REGIOSELECTIVITY [J].

GAREGG, PJ ;

HULTBERG, H .

CARBOHYDRATE RESEARCH, 1981, 93 (01) :C10-C11

[3] The effects of oligosaccharide stereochemistry on the physical properties of aqueous synthetic glycolipids [J].

Hato, M ;

Minamikawa, H .

LANGMUIR, 1996, 12 (06) :1658-1665

[4] ACCEPTOR SUBSTRATE RECOGNITION BY N-ACETYLGLUCOSAMINYLTRANSFERASE-V - CRITICAL ROLE OF THE 4''-HYDROXYL GROUP IN BETA-D-GLCPNAC-(1-)2)-ALPHA-D-MANP(1-)6)-BETA-D-GLCP-OR [J].

KANIE, O ;

CRAWLEY, SC ;

PALCIC, MM ;

HINDSGAUL, O .

CARBOHYDRATE RESEARCH, 1993, 243 (01) :139-164

[5] SYNTHETIC GLYCOCONJUGATES .2. NORMAL-PENTENYL GLYCOSIDES AS CONVENIENT MEDIATORS FOR THE SYNTHESES OF NEW TYPES OF GLYCOPROTEIN MODELS [J].

NISHIMURA, SI ;

MATSUOKA, K ;

FURUIKE, T ;

ISHII, S ;

KURITA, K ;

NISHIMURA, KM .

MACROMOLECULES, 1991, 24 (15) :4236-4241

[6] FACILE PREPARATION OF 1,6-ANHYDRO-2-AZIDO-3-O-BENZYL-2-DEOXY-BETA-D-GLUCOPYRANOSE AND ITS 4-O-SUBSTITUTED DERIVATIVES [J].

SAKAIRI, N ;

TAKAHASHI, S ;

WANG, F ;

UENO, Y ;

KUZUHARA, H .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1994, 67 (06) :1756-1758

[7] ANTITUMOR EFFECT OF HEXA-N-ACETYLCHITOHEXAOSE AND CHITOHEXAOSE [J].

SUZUKI, K ;

MIKAMI, T ;

OKAWA, Y ;

TOKORO, A ;

SUZUKI, S ;

SUZUKI, M .

CARBOHYDRATE RESEARCH, 1986, 151 :403-408

[8] Phase transition in glycolipid monolayers induced by attractions between oligosaccharide head groups [J].

Tamada, K ;

Minamikawa, H ;

Hato, M ;

Miyano, K .

LANGMUIR, 1996, 12 (06) :1666-1674

[9] LARGE-SCALE PREPARATION OF N,N'-DIACETYLCHITOBIOSE BY ENZYMATIC DEGRADATION OF CHITIN AND ITS CHEMICAL MODIFICATIONS [J].

TERAYAMA, H ;

TAKAHASHI, S ;

KUZUHARA, H .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1993, 12 (01) :81-93

[10]

UMINO A, UNPUB J CARBOHYDR CH