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M Kiso

Publications and source records attributed to M Kiso.

198 records · Page 11Linked to original sources
PubMed1982

Synthesis and biological activity of O-N-acetyl-beta-muramoyl-L-alanyl-D-isoglutamine)-(1 leads to 6)-2-acylamino-2-deoxy-D-glucoses.

Benzoylation of benzyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-alpha-D-glucopyranoside, benzyl 2-deoxy-2-(DL-3-hydroxytetradecanoylamino)-4,6-O-isopropylidene-alpha-D-glucopyranoside, and benzyl 2-deoxy-4,6-O-isopropylidene-2-octadecanoylamino-beta-D-glucopyranoside, with subsequent hydrolysis of the 4,6-O-isopropylidene group, gave the corresponding 3-O-benzoyl derivatives (4, 5, and 7). Hydrogenation of benzyl 2-acetamido-4,6-di-O-acetyl-2-deoxy-3-O-[D-1-(methoxycarbonyl)ethyl]-alpha-D-glucopyranoside, followed by chlorination, gave a product that was treated with mercuric actate to yield 2-acetamido-1,4,6-tri-O-acetyl-2-deoxy-3-O-[D-1-(methoxy-carbonyl)ethyl]-beta-D -glucopyranose (11). Treatment of 11 with ferric chloride afforded the oxazoline derivative, which was condensed with 4, 5, and 7 to give the (1 goes to 6)-beta-linked disaccharide derivative 13, 15, and 17. Hydrolysis of the methyl ester group in the compounds derived from 13, 15, and 17 by 4-O-acetylation gave the corresponding free acids, which were coupled with L-alanyl-D-isoglutamine benzyl ester, to yield the dipeptide derivatives 19-21 in excellent yields. Hydrolysis of 19-21, followed by hydrogenation, gave the respective O-(N-acetyl-beta-muramoyl-L-alanyl-D-isoglutamine)-(1 goes to 6)-2-acylamino-2-deoxy-D-glucoses in good yields. The immuno-adjuvant activity of these compounds was examined in guinea-pigs.

Acetylmuramyl-Alanyl-Isoglutamine↗
PubMed1981

Synthesis of carbohydrate analogs (positional, configurational, and optical) of n-acetylmuramoyl-L-alanyl-D-isoglutamine, and their immunoadjuvant activities.

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.

Acetylmuramyl-Alanyl-Isoglutamine↗
PubMed1981

Adjuvant activity of 6-amino-6-deoxy-muramyldipeptides and their acylamino derivatives on the induction of delayed hypersensitivity to azobenzenearsonate-N-acetyl-L-tyrosine in guinea pigs.

The 6-amino-6-deoxy-N-acetylmuramyldipeptides and their 6-acylamino derivatives were shown to be active as adjuvants on the induction of delayed-type hypersensitivity to azobenzenearsonate-N-acetyl-l-tyrosine in guinea pigs. However, 6-acylamino-6-deoxy-N-(acyl)muramyldipeptides were inactive as adjuvants.

Acetylmuramyl-Alanyl-Isoglutamine↗
PubMed1981

Adjuvant activity of carbohydrate analogs of N-acetylmuramyl-L-alanyl-D-isoglutamine on the induction of delayed-type hypersensitivity to azobenzenearsonate-N-acetyl-L-tyrosine in guinea pigs.

The adjuvant activity of 29 kinds of carbohydrate analogs of N-acetylmuramyl-L-alanyl-D-isoglutamine on the induction of delayed-type hypersensitivity to azobenzenearsonate-N-acetyl-L-tyrosine was examined in guinea pigs. It was found that the D-manno- and D-galacto-type muramyldipeptides were as active as the D-gluco-type muramyldipeptide (MDP). The structural requirement of the carbohydrate moiety of analogs of N-acetylmuramyl-L-alanyl-D-isoglutamine is discussed.

Acetylmuramyl-Alanyl-Isoglutamine↗
PubMed1976

Synthesis of prumycin and related compounds.

Prumycin (1) and related compounds have been synthesized from benzyl 2-(benzyloxycarbonyl)amino-2-deoxy-5,6-O-isopropylidene-beta-D-glucofuranoside (4). Benzoylation of 4, followed by deisopropylidenation, gave benzyl 3-O-benzoyl-2-(benzyloxycarbonyl)amino-2-deoxy-beta-D-glucofuranoside (6), which was converted, via oxidative cleavage at C-5-C-6 and subsequent reduction, into the related benzyl beta-D-xylofuranoside derivative (7). Benzylation of 3-O-benzoyl-2-(benzyloxycarbonyl)-amino-2-deoxy-D-xylopyranose (8), derived from 7 by hydrolysis, afforded the corresponding DERIVATIVES (9,11) of beta-and alpha-D-xylopyranoside, and compound 7 as a minor product. Treatment of benzyl 3-O-benzoyl-2(benzyloxycarbonyl)amino-2-deoxy-4-O-mesyl-beta-D-xylopyranoside (10), formed by mesylation of 9, with sodium azide in N,N-dimethylformamide gave benzyl 4-azido-3-O-benzoyl-2-(benzyloxycarbonyl)amino-2,4-dideoxy-alpha-L-arabinopyranoside (13), which was debenzoylated to compound 14. Selective reduction of the azide group in 14, and condensation of the 4-amine with N-[N-benzyloxycarbonyl)-D-alaninoyloxy]succinimide, gave the corresponding derivative (15) of 1. Reductive removal of the protecting groups of 15 afforded 1. Prumycin analogs were also synthesized from compound 14. Evidence in support of the structures assigned to the new derivatives is presented.

Aminoglycosides↗
PubMedDate not supplied

Antiviral and immunomodulating activities of chemically synthesized lipid A-subunit analogues GLA-27 and GLA-60.

Biological and antiviral activities of chemically synthesized lipid A-subunit analogues, GLA-27 and GLA-60, were investigated with respect to defense mechanisms such as macrophage and natural killer (NK) cell activation and interferon (IFN)-inducing activity. GLA-27, a 4-O-phosphono-D-glucosamine derivative carrying 3-O-tetradecanoyl (C14) and 2-N-3-tetradecanoyloxytetradecanoyl (C14-O-(C14] group, and GLA-60, a similar analogue carrying 3-O-linked C14-O-(C14) and 2-N-linked 3-hydroxytetradecanoyl (C14-OH) groups, strongly inhibited the formation of pox tail lesions and the growth of vaccinia virus at the tail lesion sites in infected mice. The antiviral activity of GLA-60 was about 1000-fold higher than that of muramyldipeptide (MDP), a representative immunomodulator. GLA-27 and GLA-60 had stronger immunomodulating activity than MDP in macrophage activation, NK cell activation and IFN-inducing activity, although it was weaker than natural lipid A. Toxic manifestations such as pyrogenicity, local Schwartzman reaction and lethality were far less pronounced for GLA-27 and GLA-60 than for natural lipid A.

Acetylmuramyl-Alanyl-Isoglutamine↗
PubMedDate not supplied

Antiherpes activity of chemically synthesized lipid A-subunit analogue GLA-60 in immunosuppressed mice.

Intraperitoneal administration of 10 micrograms GLA-60, a chemically synthesized lipid A analogue, to mice one day after treatment with 200 mg/kg of cyclophosphamide (CY) significantly increased the number of macrophages, lymphocytes and polymorphonuclear leukocytes (PMNs) in the peritoneal cavity. The intrinsic antiviral activity of macrophages against herpes simplex virus type 1 (HSV-1) as well as natural killer (NK) activity against YAC-1 target cells was stimulated by administration of GLA-60 to CY-immunosuppressed mice. When the mice were administered GLA-60 prior to HSV-1 infection, virus growth was inhibited and the mortality rate of infected mice was reduced. Thus, GLA-60 is a potent immunomodulator achieving its antiviral action through enhancement of nonspecific host defense mechanisms. Combined treatment of GLA-60 with the antiviral agent acyclovir (ACV) resulted in greater protection against HSV-1 in the CY-immunosuppressed mice than did single treatment with either GLA-60 or ACV.

Animals↗