共查询到20条相似文献,搜索用时 15 毫秒
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Akira Hasegawa Yoshimi Kaneda Yasuhiko Goh Kaoru Nishibori Makoto Kiso Ichiro Azuma 《Carbohydrate research》1981,94(2):143-163
2-Acetamido-2-deoxy-4- and -6-O-(d-2-propanoyl-l-alanyl-d-isoglutamine)-d-glucopyranose, 2-acetamido-2-deoxy-3-O-(d-2-propanoyl-l-alanyl-d-isoglutamine)-d-allopyranose, -d-gulopyranose, -d-galactopyranose, -d-mannopyranose, and -l-idopyranose, and 3-O-(d-2-propanoyl-l-alanyl-d-isoglutamine)-d- and -l-glucopyranose were synthesized, in order to clarify the structural requirements for the immunoadjuvant activity of the carbohydrate moiety in N-acetylmuramoyl-l-alanyl-d-isoglutamine. Immunoadjuvant activity of the N-acetylmuramoyl-dipeptide analogs was examined in guinea-pigs. 相似文献
3.
Deprotection of the fully blocked disacharide allyl O-(2-amino-4,6-O-benzylidene-3-O-[(R)-1-carboxyethyl]-2-deoxy-beta-D-glucopyranosyl-1',2-lactam)-(1-->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-beta-D-glucopyranoside by selective de-O-allylation and parallel removal of the benzylidene and O-benzyl groups is described. The resulting beta-muramyl lactam-(1-->4)-GlcNAc disaccharide is characterised as the per-O-acetylated derivative by 1H and 13C NMR spectroscopy and X-ray structure analysis. Conformational analysis about glycosidic bond of repeating units of bacterial spore cortex is based on experimental data and molecular modelling. 相似文献
4.
Synthesis of some new analogs of the immunoadjuvant glycopeptide MDP (N-acetyl-muramyl-L-alanyl-D-isoglutamine) 总被引:3,自引:0,他引:3
P Lefrancier M Derrien I Lederman F Nief J Choay E Lederer 《International journal of peptide and protein research》1978,11(4):289-296
In our continued efforts to elucidate the relationship between the structure and the immunoadjuvant, antiinfectious or mitogenic activity of N-acetyl-muramyl-L-alanyl-D-isoglutamine (MDP), we report the synthesis of 11 new analogs. Five of them present some modifications in the N-acetyl-muramyl moiety. 相似文献
5.
The disaccharide-dipeptide N-acetyl-beta-D-glucosaminyl-(1----4)-N-acetylmuramyl-L-alanyl-D-isog lut amine has been obtained by an enzymatic degradation of the peptidoglycan of Actinomadura R39. The peptidoglycan was hydrolyzed successively by the three following enzymes: lysozyme, DD-carboxypeptidase from Streptomyces albus G and gamma-D-glutamyl-meso-diaminopimelate endopeptidase I from Bacillus sphaericus 9602. The by-products of the last reaction were eliminated by successive ion-exchange and gel-permeation chromatographies. Both chemical analysis and mass spectrometry show that the resulting disaccharide-dipeptide is a pure compound. 相似文献
6.
Iu E Tsvetkov N E Ba?ramova L V Bakinovski? N K Kochetkov N F Iankina 《Bioorganicheskaia khimiia》1986,12(9):1213-1224
Methyl glycoside of the tetrasaccharide GlcNAc(beta 1-2)Rha(alpha 1-2)Rha(alpha 1-3)Rha, which represents a repeating unit of the basic chain of Shigella flexneri O-antigenic polysaccharides, was synthesized using acylated monosaccharide synthons. A dimer of the repeating unit, octasaccharide [GlcNAc(beta 1-2)Rha(alpha 1-2) Rha(alpha 1-3)Rha(alpha 1-3)]2-OMe was obtained by TrClO4-catalyzed condensation of two tetrasaccharide blocks. 相似文献
7.
Synthesis of heptasaccharide and nonasaccharide analogues of the lentinan repeating unit 总被引:1,自引:0,他引:1
The allyl glycoside beta-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-[beta-D-Glcp-(1-->6)]-beta-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-[beta-D-Glcp-(1-->6)]-alpha-D-Glcp (18) and the acetonyl glycoside of beta-D-Glcp-(1-->3)-[beta-D-Glcp-(1-->6)]-beta-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-[beta-D-Glcp-(1-->6)]-beta-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-[beta-D-Glcp-(1-->6)]-alpha-D-Glcp (28) were synthesized as analogues of the lentinan heptaose repeating unit. 4,6-O-Benzylidenated monosaccharide donor 3 and 4,6-O-benzylidenated tetrasaccharide acceptor 14 were used to ensure the beta-linkage in the synthesis of 18, while 4,6-O-benzylidenated disaccharide acceptor 20, and 4,6-O-benzylidenated disaccharide donors 21 and 24 were used to ensure the beta-linkage in the synthesis of 28. 相似文献
8.
A highly concise and effective synthesis of the mannose octasaccharide repeating unit of the cell-wall mannan of Trichophyton mentagrophytes and T. rubrum was achieved via 6-O-glycosylation of a tetrasaccharide acceptor with a tetrasaccharide donor, followed by deprotection. The key tetrasaccharide (11) was constructed by selective 6-O-glycosylation of allyl 3,4-di-O-benzoyl-alpha-D-mannopyranosyl-(1-->6)-2,3,4-tri-O-benzoyl-alpha-D-mannopyranoside with 6-O-acetyl-2,3,4-tri-O-benzoyl-alpha-D-mannopyranosyl trichloroacetimidate, then with 2,3,4,6-tetra-O-benzoyl-alpha-D-mannopyranosyl trichloroacetimidate. The tetrasaccharide acceptor (13) was obtained by selective 6-O-deacetylation of 11, while the tetrasaccharide donor 12 was obtained by deallylation of 11, followed by trichloroacetimidation. 相似文献
9.
beta-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-[beta-D-Glcp-(1-->3)-beta-D-Glcp-(1-->6)]-beta-D-Glcp (18) and the allyl glycoside of beta-D-Glcp-(1-->3)-[beta-D-Glcp-(1-->6)]-beta-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)[-beta-D-Glcp-(1-->6)]-alpha-D-Glcp (29) were synthesized as the analogues of the lentinan repeating heptaose by building the pentasaccharide backbones first, followed by attaching the side chains. 4,6-O-benzylidenated mono-13 or disaccharide 8 were used as the acceptor to ensure the beta linkage in the synthesis of 18, while 4,6-O-benzylidenated disaccharides 21 and 23 were used as the donor and acceptor, respectively, to ensure the beta linkage in the synthesis of 29. 相似文献
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11.
Akira Hasegawa Eiji Tanahashi Yasuhiko Goh Makoto Kiso Ichiro Azuma 《Carbohydrate research》1981,92(1):75-84
Five carbohydrate analogs of N-acetylmuramoyl-l-alanyl-d-isoglutamine have been synthesized from benzyl 2-acetamido-2-deoxy-3-O-[d-1-(methoxycarbonyl)ethyl]-α-d-glucopyranoside (1) and the corresponding 6-O-benzoyl derivative (2). Chlorination of 1 and 2 with triphenylphosphine in carbon tetrachloride gave the 4,6-dichloro compound 3 and the 6-O-benzoyl-4-chloro compound (4), which were treated with tributyltin hydride, to yield benzyl 2-acetamido-2,4,6-trideoxy-3-O-[d-1-(methoxycarbonyl)ethyl]-α-d-xylo-hexopyranoside (6) and benzyl 2-acetamido-6-O-benzoyl-2,4-dideoxy-3-O-[d-1-(methoxycarbonyl)ethyl]-α-d-xylo-hexopyranoside (7), respectively. Methanesulfonylation of 8, derived from 7 by debenzoylation, gave the 6-methanesulfonate, which underwent displacement with azide ion to afford benzyl 2-acetamido-6-azido-2,4,6-trideoxy-3-O-[d-1-(methoxycarbonyl)ethyl]-α-d-xylo-hexopyranoside (10). Hydrolysis of the methyl ester group in compounds 3, 5 (debenzoylated 4), 6, 8, and 10 gave the corresponding free acids, which were coupled with l-alanyl-d-isoglutamine benzyl ester, to yield the dipeptide derivatives in excellent yields. Hydrogenation of the dipeptide derivatives thus obtained gave the five carbohydrate analogs of N-acetylmuramoyl-l-alanyl-d-isoglutamine, respectively, in good yields. The immunoadjuvant activity of the N-acetylmuramoyl-dipeptide analogs was examined. 相似文献
12.
The 8-methoxycarbonyloctyl glycoside of the tetrasaccharide hapten, O-α-l-rhamnopyranosyl-(1→2)-O-α-l-rhamnopyranosyl-(1→3)-O-α-l-rhamnopyranosyl-(1→ 3)-2-acetamido-2-deoxy-β-d-glucopyranoside and the trisaccharide glycoside 8-methoxycarbonyloctyl O-α-l-rhamnopyranosyl-(1→3)-O-α-l-rhamnopyr-anosyl-(1→3)-2-acetamido-2-deoxy-β-d-glucopyranoside were synthesized by sequential Koenigs-Knorr reactions from monosaccharide units. The tetrasaccharide represents the complete skeletal repeating unit of Shigella flexneri serogroup Y lipopolysaccharide. Both oligosaccharide haptens are functionalized for covalent attachment to proteins, cell surfaces, and solid supports. 1H-N.m.r. evidence for the conformations of these oligosaccharides in solution is presented and shown to be consistent with predictions based on the exo-anomeric effect 相似文献
13.
Hernout O Berthoin K Delattre I Tulkens PM Carryn S Marchand-Brynaert J 《Bioorganic & medicinal chemistry letters》2007,17(21):5758-5762
Four small molecular receptors of vancomycin have been designed to make part of a novel biosensor device based on the FTIR-ATR detection: N-Boc (2a) or N-Ac (2b)-6-aminocaproyl-D-Ala-D-Ala and N-Boc (3a) or N-Ac (3b)-6-aminocaproyl-D-Ala-d-Ser. Using an original microbiological approach to assess the competition of compounds with the natural target of vancomycin in bacteria, EC(50) values of 6.3-8.0 x 10(-5)M (2a-b) and 7.1-9.3 x 10(-4)M (3a-b) were determined. Vancomycin:2b complex was characterized by MS. 相似文献
14.
Synthesis of the trisaccharide, allyl α-l-rhamnopyranosyl-(1→3)-2-acetamido-2-deoxy-β-d-glucopyranosyl-(1→4)-α-l-rhamnopyranoside related to O-chain glycans isolated from the deaminated LPSs of Klebsiella pneumoniae serotype 012, was achieved through condensation of suitably synthesized disaccharide, allyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-d-glucopyranosyl-(1→4)-2,3-di-O-benzoyl-α-l-rhamnopyranoside and donor, ethyl 2,3,4-tri-O-acetyl-1-thio α-l-rhamnopyranoside starting from l-rhamnose and d-glucosamine hydrochloride. The trisaccharide can be utilized for the synthesis of neoglycoconjugates for use as a synthetic vaccine by coupling it with a suitable protein after deprotection. Various regio- and stereoselective protecting group strategies have been carefully considered, as protecting groups can influence the reactivity of the electrophile and nucleophile in glycosylation reactions on the basis of steric and electronic requirements. 相似文献
15.
Ranga Rao Ravu Ying-Lien Chen Melissa R. Jacob Xuewen Pan Ameeta K. Agarwal Shabana I. Khan Joseph Heitman Alice M. Clark Xing-Cong Li 《Bioorganic & medicinal chemistry letters》2013,23(17):4828-4831
Miltefosine is an alkylphosphocholine that shows broad-spectrum in vitro antifungal activities and limited in vivo efficacy in mouse models of cryptococcosis. To further explore the potential of this class of compounds for the treatment of systemic mycoses, nine analogs (3a?3i) were synthesized by modifying the choline structural moiety and the alkyl chain length of miltefosine. In vitro testing of these compounds against the opportunistic fungal pathogens Candida albicans, Candida glabrata, Candida krusei, Aspergillus fumigatus, and Cryptococcus neoformans revealed that N-benzyl-N,N-dimethyl-2-{[(hexadecyloxy)hydroxyphosphinyl]oxy}ethanaminium inner salt (3a), N,N-dimethyl-N-(4-nitrobenzyl)-2-{[(hexadecyloxy)hydroxyphosphinyl]oxy}ethanaminium inner salt (3d), and N-(4-methoxybenzyl)-N,N-dimethyl-2-{[(hexadecyloxy)hydroxyphosphinyl]oxy}ethanaminium inner salt (3e) exhibited minimum inhibitory concentrations (MIC) of 2.5–5.0 μg/mL against all tested pathogens, when compared to miltefosine with MICs of 2.5–3.3 μg/mL. Compound 3a showed low in vitro cytotoxicity against three mammalian cell lines similar to miltefosine. In vivo testing of 3a and miltefosine against C. albicans in a mouse model of systemic infection did not demonstrate efficacy. The results of this study indicate that further investigation will be required to determine the potential usefulness of the alkylphosphocholines in the treatment of invasive fungal infections. 相似文献
16.
Synthesis, mass spectral characterization and immunoadjuvant activity of some novel lipophilic derivatives of muramyl dipeptides 总被引:1,自引:0,他引:1
R K Jain C M Gupta R K Saxena R P Saxena K C Saxena R Shukla N Anand C E Costello 《Chemistry and physics of lipids》1986,41(3-4):237-264
Some novel lipophilic derivatives of N-acetylmuramyl-L-alanyl-D-isoglutamine (MDP) have been prepared and rigorously evaluated by spectroscopic means. Fast atom bombardment and field desorption mass spectrometry provided information about both molecular weight and structural detail. The new MDP derivatives have been tested in guinea pigs for immunoadjuvant activity using egg albumin as the model antigen. Amongst these derivatives, 6-O-[3-(5-cholesten-3 beta-yloxycarbonyl) propionyl]-N-acetylmuramyl-L-alanyl-D-isoglutamine (CSMDP), 6-O-[3-1,2-dipalmitoyl-sn-glycero-3-carbonyl) propionyl]-N-acetylmuramyl-L-alanyl-D-isoglutamine (GSMDP) and N-palmitoyl muramyl-L-alanyl-D-isoglutamine (PMDP) possessed significantly better activity than MDP, as judged by the antigen-specific antibody and delayed hypersensitivity responses in the immunized animals. In addition, CSMDP was found to induce strong delayed hypersensitivity response even in saline. These three active compounds were also tested for their pyrogenic response in rabbits, and were found to be lesser pyrogenic than MDP. Some of these MDP derivatives hold promise as adjuvants in immunization. 相似文献
17.
A pentasaccharide, beta-D-Man-(1-->2)-[beta-D-GlcNAc-(1-->4)]-alpha-L-Rha-(1-->4)-alpha-L-Rha-(1-->4)-alpha-L-Rha-1-OC8H17, representing the repeating unit of latosillan, was convergently synthesized from the building blocks, ethyl 2,3-O-isopropylidene-1-thio-alpha-l-rhamnopyranoside, 2-O-acetyl-3,4,6-tri-O-benzyl-beta-d-glucopyranosyl trichloroacetimidate, and 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-beta-d-glucopyranosyl trichloroacetimidate under standard glycosylation conditions. The target pentasaccharide showed acceptable differentiation-inducing activity on HL-60 cell lines at the dosages of 10-50 microg/mL. 相似文献
18.
As part of a search for estradiol derivatives designed for conjugation to carboxyl or amine functions of anti-cancer agents or suitable derivatives thereof, estradiol analogs with side chains at the C-16 or -17 position were prepared for biological assay. These analogs include several which have a substituted nitrogenous function at C-17. The avidity of some of these analogs for binding to estrogen receptor was found to be of a low order. 相似文献
19.
Some aromatic prostaglandin analogs, having a benzene (2a, 2b) and a dimethoxybenzene (1) ring in place of the cyclopentane moiety, have been synthesized. The key intermediates in the syntheses were lactols 9 and 5, which were elaborated to the final products via two olefination reactions. Compound 2b was twice as potent as phenylbutazone and nine times as potent as aspirin in inhibiting prostaglandin synthetase activity. 相似文献
20.
Some aromatic prostaglandin analogs, having a benzene (2a, 2b) and a dimethoxybenzene (1) ring in place of the cyclopentane moiety, have been synthesized. The key intermediates in the syntheses were lactols 9 and 5, which were elaborated to the final products via two olefination reactions. Compound 2b was twice as potent as phenylbutazone and nine times as potent as aspirin in inhibiting prostaglandin synthetase activity. 相似文献