• Title/Summary/Keyword: deacetylation

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Inhibitory effect of chitosan oligosaccharides on the growth of tumor cells

  • Kim, Se-Kwon;Nam, Mi-Young;Nam, Kyung-Soo
    • Proceedings of the Korean Society of Fisheries Technology Conference
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    • 2000.05a
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    • pp.416-417
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    • 2000
  • Chitin, a poly $\beta$-(1longrightarrow14)-N-acetyl-D-glucosamine, is best known as a cell wall component of fungi and as a skeletal materials of invertebrates. Chitosan is derived from chitin by deacetylation in the presence of alkali. Chitosan has been developed as new physiological materials since it possesses antibacterial activity, hypocholesterolemic activity and antihypertensive action. However, the actions of chitosan in vivo still remain ambiguous as the physiological functional properties because most animal intestines, especially the human gastrointestinal tract, do not possess enzyme such as chitosanase which directly degrade the $\beta$-glucosidic linkage in chitosan, and consequently the unbroken polymers may be poorly absorbed into the human intestine. Therefore, recent studies as chitosan have attracted interest for chitosan oligosaccharides, because the oligosaccharides process not only water-soluble property but also versatile functional properties such as antitumor activity, immune-enhancing effects, enhancement of protective effects against infection with some pathogens in mice and antimicrobial activity (Kingsnorth et al., 1983, Mori et al., 1997). (omitted)

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Antimicrobial effect of chitosan oligosaccharides, prepared under ultrafiltration membrane bioreactor, against Vibrio spp. causing fish diseases

  • Lee, Jehee;Jeon, You-Jin;Heo, Moon-Soo;Lee, Ki-Wan;Song, Choon-Bok;Yeo, In-Kyo;Yang, Byung-Gyoo;Kim, Se-Kwon
    • Proceedings of the Korean Society of Fisheries Technology Conference
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    • 2001.10a
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    • pp.151-152
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    • 2001
  • Chitin, a polymer of N-acetylglucosamine ($\beta$-1,4 linked 2-acetamido-D-glucose), is a cellulose-like biopolymer present richly in the exoskeleton of crustaceans and in cell walls of fungi, insects and yeast. Chitosan is derived from chitin by deacetylation, to different degrees, in the presence of alkali. [l]. Recent studies for chitin and chitosan have been concentrated in bioactivities such as antitumor activity, immuno-enhancing effects, enhancing protective effects against infection with some pathogens in mice, and antimicrobial activeity [2]. (omitted)

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Syntheses of Idarubicin Analogues Containing a Glucose or Galactose Moiety as a Glycone

  • Rho, Young-S.;Park, Ran;Kim, Seon-Young;Yoo, Dong-Jin
    • Bulletin of the Korean Chemical Society
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    • v.31 no.1
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    • pp.69-74
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    • 2010
  • The new idarubicin analogues (12 and 13) with a glucose or galactoseas as a glycone were synthesized from daunomycin (2). (+)-4-Demethoxydaunomycinone (6) obtained from reaction of 2 with $AlCl_3$ was converted to 4-trifluoromethanesulfonyl daunomycinone (7) through reaction with trifluoromethanesulfonic anhydride. The treatment of 7 with 1,1-bis-(diphenylphospino)ferrocene/$Pd(OAc)_2$ in triethylamine/formic acid/dioxane provided the idarubicinone (5b). Glycosylation of 7-hydroxy group of 5b with two kinds of tetraacetyl pyranosyl halide (8 and 9) by a modified Koenigs-Knorr procedure and then deacetylation using aqueous 0.1 N LiOH solution and amberlite cationic resin gave the objective materials. The in vitro MTT assay of the analogues (12b and 13a) in comparison with idarubicin (5a) on peripheral blood human promyelocytic-leukemia cell line and human breast cancer cell line were also described.

Synthesis of the 2'-Azidoethyl Trisaccharide, 6d-altroHepp-GlcNAc-Gal Hapten, an O-Antigenic Repeating Unit of Campylobacter jejuni Serotypes O:23 and O:36

  • Yun, Mi-Kyung;Shin, Jeong E. Nam
    • Bulletin of the Korean Chemical Society
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    • v.29 no.7
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    • pp.1315-1319
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    • 2008
  • A trisaccharide, 6d-Altro-Hepp$\alpha$ (1$\rightarrow$3) GlcNAc$\beta$ (1$\rightarrow$3) Gal$\alpha$ (1$\rightarrow$$OCH_2CH_2N_3$, as an O-antigenic repeating unit of Campylobacter jejuni serotypes O:23 and O:36, was synthesized. Coupling of the 6d-altro-Hepp$\alpha$ (1$\rightarrow$3) GlcNAc$\beta$ (1$\rightarrow$SEt donor with Gal$\alpha$ (1${\rightarrow}OCH_2CH_2Cl$ acceptor in the presence of NIS-TfOH promoter afforded the trisaccharide having the $\beta$ (1$\rightarrow$3) Gal linkage. $\beta$ -Stereospecificity and the desired regioselectivity for the 3-OH Gal are obtained. Subsequent hydrogenation, acetylation, azide displacement, hydrazinolysis, Nacetylation, and finally deacetylation furnished the title trisaccharide hapten for further glycoconjugation.

Effect of Chitosan Treatment on the Hand of Nonwoven Fabric (키토산 처리에 의한 부직포의 태 변화)

  • 신윤숙;손경희
    • Korean Journal of Human Ecology
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    • v.1 no.2
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    • pp.119-128
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    • 1998
  • Nonwoven fabrics for diaper coverstock were treated with chitosan solution by pad-dry method. Two chitosans of different molecular weigh(Mw) with similar degree of deacetylation(DDA) were used: Mw 1,800(chitosan oligomer, DDA 84%). Effect of chitosan treatment on the mechanical properties was investigated using KES-FB system. Primary hand values were calculated from mechanical properties using the same equation as the men's suiting equation with minor modification, and total hand values were calculated using new KN-5LNW equation for nonwoven fabrics developed by Kawabata et al. Increase in chitosan treatment concentration increased B, 2HB, WT, LT and RC, and decreased WC continuously. Chitosan treatment affected other mechanical properties regardless of molecular weight. Considering primary hand values obtained from mechanical properties, it was found that chitosan of Mw 180,000 and chitosan oligomer provided softer, smoother, and more bulky at below 0.05% and above 0.5% treatment concentration respectively. Samples treated with 1.0% chitosan oligomer solution, and 0.01% chitosan solution of Mw 180,000 showed the best total hand values. (Korean J Human Ecology 1(2):119∼128, 1998)

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Biofonctional properties of Chitosan Mcmbrancs Grafted with 2-(methacryloyloxy)-ethyl-2-(trimethylammonium) ethyl phosphate

  • Lee, M.K.;Park, H.S.;Park, S.M.
    • Proceedings of the Membrane Society of Korea Conference
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    • 1995.04a
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    • pp.46-47
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    • 1995
  • Chitosan, an unbranched (1-4)-linked-2-amino-2-deoxy-$\beta$-D-glucan, is prepared by chemical N-deacetylation of chitin, which is the main structure element of the cuticles of crab, shrimp, and insects, and is found in the cell walls of bacteria. It has the same main chain in its molecule like that of natural heparin. Heparin, an anionic polysaccharide, is the best of anticoagulants that have been found so far. In this study, to improve the blood compatibility of chitosan, 2-(methacrylovloxy)-ethyl-2-(trimethylammonium)ethyl phosphate(MTP) with phospholipid polar groups was grafted on the chitosan membranes and the biochemical properties the MTP-grafted chitosan membranes were investigated.

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Isolation and Characterization of Chitin from Crab Shell (게 껍질로부터 Chitin의 분리 및 특성 규명)

  • 김성배;박태경
    • KSBB Journal
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    • v.9 no.2
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    • pp.174-179
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    • 1994
  • Chitin was isolated from crab shell wastes and characterized for its chemical and physical properties. White powdered chitin was obtained through demineralizaticn, deproteinization and decoloration process. The contents of inorganics was less than 0.5%, whereas protein and lipid were almost removed. The results of IR spectroscopic analysis for the isolated chitin showed similar characteristics with that of Sigma product. Degree of deacetylation of purified chitin was significantly higher than Sigma product and viscosity average molecular weights was $2.3{\times}10^5~3.2{\times}10^5$. SEM analysis showed that the obtained chitin had the fibril shaped morphology.

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Antimicrobial Finish of Nonwoven Fabric by Treatment with Chitosan (키토산을 이용한 부직포의 항미생물가공)

  • Younsook Shin;Kyunghye Min
    • Textile Coloration and Finishing
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    • v.10 no.3
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    • pp.50-56
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    • 1998
  • Nonwoven fabric was treated with chitosan solution to impart antimicrobial activities by pad-dry method. Antimicrobial activity was measured by Shake Flask Method. Two chitosans of different molecular weight(Mw) with similar degree of deacetylation(DDA) were used : ca. 1,800(chitosan oligomer : DDA 84%) and 180,000(DDA 86%). Chitosan oligomer displayed high antimicrobial activity against P. vulgaris at 0.01%, S. aureus and E. coli at 0.05% treatment concentration, shelving above 90% of reduction rate. Chitosan of Mw 180,000 was effective against S. aureus, E. coil and P. vulgaris at 0.05% treatment concentration, showing almost 100% reduction rate. While chitosan of Mw 180,000 shelved reduction rate above 75% against K. pneumoniae and P. aeruginosa at 0.5% treatment concentration, chitosan oligomer was not effective against them. Fabrics become stiffer and less air permeable as treatment concentration increases. Liquid strike-through time of the sample treated with 0.5% chitosan oligomer solution (3.0 sec) was comparable with a hydrophilic finished sample commercially available(2.6 sec).

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In Vitro Effect of Aspalatone on Platelet Aggregation and Thromboxane Production in Human Platelet Rich Plasma

  • Suh, Dae-Yeon;Han, Byung-Hoon
    • Biomolecules & Therapeutics
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    • v.4 no.2
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    • pp.122-126
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    • 1996
  • In vitro inhibitory effect of aspalatone ((3-(2-methyl-4-pyronyl)]-2-acetyloxybenzoate) on collagen-, ADP-, and epinephrine-induced platelet aggregation in human platelet rich plasma (PRP) was compared with the effects of reference drugs (acetylsalicylic acid, cilostazol and ticlopidine). Aspalatone inhibited time and dose dependently human platelet aggregation induced by collagen; relative potency was in the order of cilostazol>acetylsalicylic acid>aspalatone>ticlopidine. Aspalatone, like acetylsalicylic acid, potently inhibited only the secondary phase of ADP-and epinephrine-induced aggregation. Thromboxane $B^2$ production evoked by collagen in human PRP was inhibited significantly and concentration-dependently by aspalatone and acetylsalicylic acid. These results were in agreement with the earlier studies in which the antiplatelet action of aspalatone was indicated to be due to the inhibition of platelet cyclooxygenase activity (Han et al., Arzneim. Forsch./Drug Res. 44(II), 1122, 1994; Suh and Han, Yakhak Hoeji 39, 565, 1995). In addition, the inhibitory activity of aspalatone on the platelet aggregation appears to be inversely related to the rate of nonspecific deacetylation of the drug in plasma.

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Purification and Seperation of Chitooligosaccharides Hydrolyzed by Chitosanolytic Enzyme (Chitosanase의 분해에 의한 Chitooligo당의 분리 정제)

  • Ryu, Byeong-Ho;Bin, Jae-Hun;Lee, Seong-Ho
    • The Korean Journal of Food And Nutrition
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    • v.8 no.1
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    • pp.43-49
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    • 1995
  • This studies were carried out to purification and seperation of chitooligosaccharides which containing excellent biological active substance. After deacetylation of chitosan (DAC%), DAC-45%, DAC-70%, DAC-95% and DAC-99% were used substrates and hydrolyzed by chitosanase (Bacillus pumilus BN-262) DAC-99% has excellent hydrolyzate which contained several chitooligosaccharides. Therefore, chitosan was hydrolyzed DAC-90 as substrate by chitosanase, and then purified and seperated of chitooligosaccharides Gel filteration and HPLC. This oligosaccharides composed with GlcN0, GlcN2, GlcN3, Glc5 and GlcN6.

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