caa a22 4500 465734464 CHVBK 20180323111751.0 cr unu---uuuuu 170327e19900701xx s 000 0 eng 10.1007/BF01073377 doi (NATIONALLICENCE)springer-10.1007/BF01073377 Synthesis of N -Acetylglucosamine derivatives as probes for specificity of chicken hepatic lectin [Elektronische Daten] [Yoshitaka Ichikawa, Reiko Lee, Yuan Lee] Syntheses of the following compounds are described: 6-(Trifluoroacetylamino)hexyl 2-acetamido-2,6-dideoxy-β-d-glucopyranoside and 2-acetamido-2-deoxy-α-d-xylopyranoside, two allyl 2-acetamido-2-deoxy-α-d-glucopyranosiduronic acid derivatives, and several allyl 2-acylamido-2-deoxy-β-d-glucopyranosides having different acyl groups. These and other compounds were used as inhibitors in the binding assay for the chicken hepatic lectin specific forN-acetylglucosamine. We found that: 1) The inhibitory potency ofN-acylglucosamine derivatives decreased progressively with increase in the size of acyl group, 2) absence of either 3-or 4-OH group ofN-acetylglucosamine lowered the binding affinity more than 100-fold, and 3) the presence of a negatively charged group (carboxylic acid) at the C-6 position did not lower the affinity. The first two items are similar to the mammalian hepatic galactose/N-acetylgalactosamine lectins, but the last item is in a strong contrast to the mammalian lectins. Glycoconjugate Journal AB, 1990 N-acetylglucosamine derivatives nationallicence chicken hepatic lectin nationallicence N-acetylglucosamine-specific lectin nationallicence XyLNAc : N-acetyl-d-xylosamine nationallicence BSA : bovine serum albumin nationallicence NeuAc : N-acetylneuraminic acid nationallicence GlcNAc34-BSA : amidino-type neoglycoprotein [6] containing on the average 34N-acetylglucosaminyl residues per BSA molecule nationallicence Ichikawa Yoshitaka Department of Biology, the Johns Hopkins University, 21218, Baltimore, MD, U.S.A. aut Lee Reiko Department of Biology, the Johns Hopkins University, 21218, Baltimore, MD, U.S.A. aut Lee Yuan Department of Biology, the Johns Hopkins University, 21218, Baltimore, MD, U.S.A. aut Glycoconjugate Journal Kluwer Academic Publishers 7/4(1990-07-01), 335-348 0282-0080 7:4<335 1990 7 10719 https://doi.org/10.1007/BF01073377 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/BF01073377 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Ichikawa Yoshitaka Department of Biology, the Johns Hopkins University, 21218, Baltimore, MD, U.S.A aut NATIONALLICENCE 700 1- Lee Reiko Department of Biology, the Johns Hopkins University, 21218, Baltimore, MD, U.S.A aut NATIONALLICENCE 700 1- Lee Yuan Department of Biology, the Johns Hopkins University, 21218, Baltimore, MD, U.S.A aut NATIONALLICENCE 773 0- Glycoconjugate Journal Kluwer Academic Publishers 7/4(1990-07-01), 335-348 0282-0080 7:4<335 1990 7 10719 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer