RESUMEN
A small series of C-cinnamoyl glycosides incorporating the phenol moiety has been prepared by reaction of glycosyl ketones with the appropriate benzaldehydes. Glycosides were tested for the inhibition of twelve mammalian isoforms of carbonic anhydrase. This is the first study in which α-CAs have been investigated for their interaction with C-glycosides, a novel carbohydrate scaffold in the design of carbonic anhydrase inhibitors. The C-cinnamoyl glycosides were generally effective CA inhibitors, with inhibition constants in the low micromolar range against CA I, II, IV, VA, VB, VI, VII, IX, XII, XIII, XIV and ineffective inhibitors of CA III. These results confirm that attaching carbohydrate moieties to CA phenol pharmacophore improves its inhibitory activity.
Asunto(s)
Inhibidores de Anhidrasa Carbónica/síntesis química , Anhidrasas Carbónicas/química , Cinnamomum zeylanicum/química , Monosacáridos/química , Animales , Inhibidores de Anhidrasa Carbónica/química , Inhibidores de Anhidrasa Carbónica/metabolismo , Anhidrasas Carbónicas/metabolismo , Glicósidos , Humanos , Isoenzimas/antagonistas & inhibidores , Isoenzimas/metabolismo , Cinética , Monosacáridos/síntesis química , Monosacáridos/metabolismo , Unión ProteicaRESUMEN
The serum fraction of latex from Hevea brasiliensis, the para rubber tree, is known to contain an endo-chitinolytic enzyme, hevamine. Herein the activity of the rubber serum towards beta-chitin is investigated. The serum contained 6 mg/mL of protein and a chitinolytic activity of 18 mU permg of protein. The optimum ratio of enzyme to chitin was 0.22 mU/mg, and the optimum substrate concentration was 60 mg/mL. The optimum pH range was pH2-4, and the optimum temperature was 45 degrees C. At these conditions both (GlcNAc)2 and GlcNAc were produced in a molar ratio of approximately 2:1. The hydrolysis of 300 mg of chitin with 64 mU of the rubber serum for 8 days under the optimum conditions gave 39 mg of GlcNAc and 108 mg of (GlcNAc)2 as determined by HPLC. Mixing the rubber serum preparation with an Aspergillus niger pectinase preparation containing beta-N-acetylhexosaminidase can be used to produce almost exclusively the GlcNAc monomer in about 50% yield.
Asunto(s)
Quitina/química , Disacáridos/síntesis química , Hevea/química , Monosacáridos/síntesis química , Extractos Vegetales/química , Aspergillus niger/enzimología , Hevea/enzimología , Modelos Moleculares , Poligalacturonasa/química , Factores de TiempoRESUMEN
Vibrio cholerae O1 LPS terminal mono- and disaccharide elements were synthesized by reduction of the azido group in several 4-amino-4,6-dideoxy-D-mannose mono- and disaccharide derivatives, followed by coupling with 2, 4-di-O-acetyl-3-deoxy-L-glycero-tetronic acid in the presence of 2-ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline. This compound represents a useful model in order to elucidate the size of the epitopes which define Ogawa and Inaba serotypes from Vibrio cholerae O1.