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Book ; Conference proceedings: 43.-Tennen-yūki-kagōbutsu-tōronkai-kōen-yōshishū / 43rd Symposium on the Chemistry of Natural Products

Kusumoto, Shoichi

Ōsaka 2001 = Symposium papers

2001

Title variant	Symposium papers // 43rd Symposium on the Chemistry of Natural Products ; The chemistry of natural products, Osaka 2001
Institution	Tennen-Yūki-Kagōbutsu-Tōronkai
Event/congress	Symposium on the Chemistry of Natural Products (43, 2001.10.02-04, Osaka) ; Tennen Yūki Kagōbutsu Tōronkai (43, 2001.10.02-04, Ōsaka)
Author's details	[organizing committee: Shoichi Kusumoto]
Language	Japanese ; English
Size	XLVI, 656 S, Ill., graph. Darst
Publisher	Osaka University
Publishing place	Ōsaka
Document type	Book ; Conference proceedings
Note	Beitr. teilw. japan., teilw. engl
Database	Library catalogue of the German National Library of Science and Technology (TIB), Hannover

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Article: Structure and synthesis of lipid A.

Kusumoto, Shoichi / Hashimoto, Masahito / Kawahara, Kazuyoshi

Advances in experimental medicine and biology

2010 Volume 667, Page(s) 5–23

MeSH term(s)	Carbohydrate Conformation ; Carbohydrate Sequence ; Escherichia coli/metabolism ; Lipid A/biosynthesis ; Lipid A/chemistry
Chemical Substances	Lipid A
Language	English
Publishing date	2010
Publishing country	United States
Document type	Journal Article
ISSN	2214-8019 ; 0065-2598
ISSN (online)	2214-8019
ISSN	0065-2598
DOI	10.1007/978-1-4419-1603-7_2
Database	MEDical Literature Analysis and Retrieval System OnLINE

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Article ; Online: Lipopolysaccharide induces raft domain expansion in membrane composed of a phospholipid-cholesterol-sphingomyelin ternary system.

Nomura, Kaoru / Maeda, Masahide / Sugase, Kenji / Kusumoto, Shoichi

Innate immunity

2011 Volume 17, Issue 3, Page(s) 256–268

Abstract: The molecular behavior and interaction of Re-type lipopolysaccharide (ReLPS) and phospholipids were investigated in two different types of model membrane systems, a pure phospholipid membrane consisting of 1,2-dielaidoyl-snglycero-3-phosphoethanolamine ( ... ...

Abstract	The molecular behavior and interaction of Re-type lipopolysaccharide (ReLPS) and phospholipids were investigated in two different types of model membrane systems, a pure phospholipid membrane consisting of 1,2-dielaidoyl-snglycero-3-phosphoethanolamine (DEPE) and a raft-forming membrane composed of equimolar DEPE, sphingomyelin (SM), and cholesterol (Chol) by solid-state NMR spectroscopy. A remarkable influence of ReLPS on the property of lipid bilayer was found by analyzing the (13)C-NMR spectra. Namely, while both liquid-ordered (L(o)) and liquid-disordered (L(d)) phases co-exist in DEPE/SM/Chol, only the L(o) phase is present in DEPE/SM/Chol/ReLPS. This clearly indicates that ReLPS induces expansion of the raft area in the raft-forming membrane. The (1)H spin-lattice relaxation times in the rotating frame T( 1ρ) (H) in the two different membranes, DEPE/ReLPS and DEPE/SM/Chol/ReLPS, indicate that the motion of DEPE is affected by the presence of ReLPS, Chol, and SM, and much faster than that of ReLPS in both membranes. The ReLPS in the raft-forming membrane, in particular, accelerated the movement of DEPE. Thus, this study shows the possibility that LPS induces the expansion of raft region and the rapid motion of the raft-forming membranes to favor molecular interactions in the animal cell membrane during innate immune recognition.
MeSH term(s)	Cell Enlargement ; Cell Membrane/physiology ; Host-Pathogen Interactions ; Immunity, Innate ; In Vitro Techniques ; Infection/immunology ; Lipopolysaccharides/chemistry ; Lipopolysaccharides/metabolism ; Lipoproteins, HDL/chemistry ; Lipoproteins, HDL/metabolism ; Magnetic Resonance Spectroscopy ; Membrane Microdomains/metabolism ; Membranes, Artificial ; Phospholipids/chemistry ; Phospholipids/metabolism ; Signal Transduction ; Sphingomyelins/chemistry ; Sphingomyelins/metabolism
Chemical Substances	Lipopolysaccharides ; Lipoproteins, HDL ; Membranes, Artificial ; Phospholipids ; Sphingomyelins ; high density lipoprotein sphingomyelin
Language	English
Publishing date	2011-02
Publishing country	United States
Document type	Comparative Study ; Journal Article ; Research Support, Non-U.S. Gov't
ISSN	1753-4267
ISSN (online)	1753-4267
DOI	10.1177/1753425910365944
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Article: Synthesis of endotoxic principle of bacterial lipopolysaccharide and its recognition by the innate immune systems of hosts.

Kusumoto, Shoichi / Fukase, Koichi

Chemical record (New York, N.Y.)

2006 Volume 6, Issue 6, Page(s) 333–343

Abstract: A new stage of endotoxin research was brought about by structure elucidation and chemical synthesis of lipid A, the lipophilic partial structure of the lipopolysaccharide (LPS) of Gram-negative bacteria. Synthetic lipid A exhibited full endotoxic ... ...

Abstract	A new stage of endotoxin research was brought about by structure elucidation and chemical synthesis of lipid A, the lipophilic partial structure of the lipopolysaccharide (LPS) of Gram-negative bacteria. Synthetic lipid A exhibited full endotoxic activity, which gave unequivocal evidence for the concept that lipid A is the active entity of endotoxin. Various lipid A analogues, as well as their radiolabeled derivatives and more complex partial structures of LPS, were also synthesized. By the use of these synthetic homogeneous preparations, not only simple studies on structure-activity relationships but precise and detailed analyses became possible on how this typical bacterial component is recognized by the innate immune receptor complex of mammalian cells.
MeSH term(s)	Animals ; Cells, Cultured ; Gram-Negative Bacteria ; Humans ; Immunity, Innate/drug effects ; Immunity, Innate/immunology ; Lipid A/chemical synthesis ; Lipid A/chemistry ; Lipid A/immunology ; Lipid A/pharmacology ; Lymphocyte Antigen 96/immunology ; Molecular Structure ; Structure-Activity Relationship ; Toll-Like Receptor 4/immunology
Chemical Substances	Lipid A ; Lymphocyte Antigen 96 ; Toll-Like Receptor 4
Language	English
Publishing date	2006
Publishing country	United States
Document type	Journal Article
ZDB-ID	2044646-9
ISSN	1528-0691 ; 1527-8999
ISSN (online)	1528-0691
ISSN	1527-8999
DOI	10.1002/tcr.20098
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Article ; Online: Key structures of bacterial peptidoglycan and lipopolysaccharide triggering the innate immune system of higher animals: Chemical synthesis and functional studies".

Kusumoto, Shoichi / Fukase, Koichi / Shiba, Tetsuo

Proceedings of the Japan Academy. Series B, Physical and biological sciences

2010 Volume 86, Issue 5, Page(s) 322–337

Abstract: Chemistry-based investigation is reviewed which led to identification of the active entities responsible for the immunostimulating potencies of peptidoglycan and lipopolysaccharide. Though these glycoconjugates which ubiquitously occur in wide range of ... ...

Abstract	Chemistry-based investigation is reviewed which led to identification of the active entities responsible for the immunostimulating potencies of peptidoglycan and lipopolysaccharide. Though these glycoconjugates which ubiquitously occur in wide range of bacteria as the essential components of their cell envelopes have long been known to enhance the immunological responses of higher animals, neither the precise chemical structures required nor the mechanism of their action had been elucidated until early 1970s. Chemical synthesis of partial structures of peptidoglycan proved N-acetylmuramyl-L-alanyl-D-isoglutamine to be the minimum structure responsible for the activity and led to later identification of its receptor protein Nod2 present in animal cells. Another active partial structure of peptidoglycan, g-D-glutamylmeso-diaminopimelic acid, and its receptor Nod1 were also identified as well. With regard to lipopolysaccharide, its glycolipid part named lipid A was purified and the structure studied. Chemically synthesized lipid A according to the newly elucidated structure exhibited full activity described for lipopolysaccharide known as endotoxin. Synthetic homogeneous lipid A and its structural analogues and labeled derivatives enabled precise studies of their interaction with receptor proteins and the mechanism of their action. Chemical synthesis of homogeneous partial structures of peptidoglycan and lipopolysaccharide gave unequivocal evidences for the concept that definite small molecular parts of these complex macromolecular bacterial glycoconjugates are specifically recognized by their respective receptors and trigger our defense system now widely recognized as innate immunity.
Language	English
Publishing date	2010
Publishing country	Japan
Document type	Journal Article ; Corrected and Republished Article
ZDB-ID	161781-3
ISSN	1349-2896 ; 0386-2208
ISSN (online)	1349-2896
ISSN	0386-2208
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Article ; Online: Key structures of bacterial peptidoglycan and lipopolysaccharide triggering the innate immune system of higher animals: chemical synthesis and functional studies.

Kusumoto, Shoichi / Fukase, Koichi / Shiba, Tetsuo

Proceedings of the Japan Academy. Series B, Physical and biological sciences

2010 Volume 86, Issue 4, Page(s) 322–337

Abstract	Chemistry-based investigation is reviewed which led to identification of the active entities responsible for the immunostimulating potencies of peptidoglycan and lipopolysaccharide. Though these glycoconjugates which ubiquitously occur in wide range of bacteria as the essential components of their cell envelopes have long been known to enhance the immunological responses of higher animals, neither the precise chemical structures required nor the mechanism of their action had been [corrected] elucidated until early 1970s. Chemical synthesis of partial structures of peptidoglycan proved N-acetylmuramyl-L-alanyl-D-isoglutamine to be the minimum structure responsible for the activity and led to later identification of its receptor protein Nod2 present in animal cells. Another active partial structure of peptidoglycan, gamma-D-glutamyl-meso-diaminopimelic acid, and its receptor Nod1 were also identified as well. With regard to lipopolysaccharide, its glycolipid part named lipid A was purified and the structure studied. Chemically synthesized lipid A according to the newly elucidated structure exhibited full activity described for lipopolysaccharide known as endotoxin. Synthetic homogeneous lipid A and its structural analogues and labeled derivatives enabled precise studies of their interaction with receptor proteins and the mechanism of their action. Chemical synthesis of homogeneous partial structures of peptidoglycan and lipopolysaccharide gave unequivocal evidences for the concept that definite small molecular parts of these complex macromolecular bacterial glycoconjugates are specifically recognized by their respective receptors and trigger our defense system now widely recognized as innate immunity.
MeSH term(s)	Acetylmuramyl-Alanyl-Isoglutamine/immunology ; Animals ; Bacteria ; Humans ; Immunity, Innate/immunology ; Lipid A/immunology ; Lipopolysaccharides/chemical synthesis ; Lipopolysaccharides/chemistry ; Lipopolysaccharides/immunology ; Peptidoglycan/chemistry ; Peptidoglycan/immunology
Chemical Substances	Lipid A ; Lipopolysaccharides ; Peptidoglycan ; Acetylmuramyl-Alanyl-Isoglutamine (53678-77-6)
Language	English
Publishing date	2010-04-27
Publishing country	Japan
Document type	Journal Article ; Review
ZDB-ID	161781-3
ISSN	1349-2896 ; 0386-2208
ISSN (online)	1349-2896
ISSN	0386-2208
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Article ; Online: Toll-like receptors of the ascidian Ciona intestinalis: prototypes with hybrid functionalities of vertebrate Toll-like receptors.

Sasaki, Naoko / Ogasawara, Michio / Sekiguchi, Toshio / Kusumoto, Shoichi / Satake, Honoo

The Journal of biological chemistry

2009 Volume 284, Issue 40, Page(s) 27336–27343

Abstract: Key transmembrane proteins in the innate immune system, Toll-like receptors (TLRs), have been suggested to occur in the genome of non-mammalian organisms including invertebrates. However, authentic invertebrate TLRs have been neither structurally nor ... ...

Abstract	Key transmembrane proteins in the innate immune system, Toll-like receptors (TLRs), have been suggested to occur in the genome of non-mammalian organisms including invertebrates. However, authentic invertebrate TLRs have been neither structurally nor functionally investigated. In this paper, we originally present the structures, localization, ligand recognition, activities, and inflammatory cytokine production of all TLRs of the ascidian Ciona intestinalis, designated as Ci-TLR1 and Ci-TLR2. The amino acid sequence of Ci-TLR1 and Ci-TLR2 were found to possess unique structural organization with moderate sequence similarity to functionally characterized vertebrate TLRs. ci-tlr1 and ci-tlr2 genes were expressed predominantly in the stomach and intestine as well as in hemocytes. Ci-TLR1 and Ci-TLR2 expressed in HEK293 cells, unlike vertebrate TLRs, were localized to both the plasma membrane and endosomes. Intriguingly, both Ci-TLR1 and Ci-TLR2 stimulate NF-kappaB induction in response to multiple pathogenic ligands such as double-stranded RNA, and bacterial cell wall components that are differentially recognized by respective vertebrate TLRs, revealing that Ci-TLRs recognize broader pathogen-associated molecular patterns than vertebrate TLRs. The Ci-TLR-stimulating pathogenic ligands also induced the expression of Ci-TNFalpha in the intestine and stomach where Ci-TLRs are expressed. These results provide evidence that the TLR-triggered innate immune systems are essentially conserved in ascidians, and that Ci-TLRs possess "hybrid" biological and immunological functions, compared with vertebrate TLRs. Moreover, it is presumed that chordate TLR ancestors also acquired the Ci-TLR-like multiple cellular localization and pathogen-associated molecular pattern recognition.
MeSH term(s)	Animals ; Cell Line ; Cell Membrane/metabolism ; Chordata ; Ciona intestinalis/cytology ; Ciona intestinalis/genetics ; Ciona intestinalis/metabolism ; Endosomes/metabolism ; Gene Expression Regulation ; Humans ; Ligands ; Molecular Sequence Data ; Phylogeny ; Protein Transport ; Species Specificity ; Substrate Specificity ; Toll-Like Receptors/chemistry ; Toll-Like Receptors/genetics ; Toll-Like Receptors/metabolism ; Tumor Necrosis Factor-alpha/metabolism
Chemical Substances	Ligands ; Toll-Like Receptors ; Tumor Necrosis Factor-alpha
Language	English
Publishing date	2009-08-03
Publishing country	United States
Document type	Journal Article
ZDB-ID	2997-x
ISSN	1083-351X ; 0021-9258
ISSN (online)	1083-351X
ISSN	0021-9258
DOI	10.1074/jbc.M109.032433
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Article: 2JC,H index: a nondestructive NMR method for differentiation of aldohexopyranosyl residues.

Oikawa, Masato / Adachi, Seiji / Kusumoto, Shoichi

Organic letters

2005 Volume 7, Issue 4, Page(s) 661–664

Abstract: A new 2J(C,H) index method is described for identification of aldohexopyranose. This method is based on a fact that 2J(C,H) values reflect the stereochemistry for glycol connectivity. Based on the observed 2J(C,H) values for galactose, glucose, and ... ...

Abstract	A new 2J(C,H) index method is described for identification of aldohexopyranose. This method is based on a fact that 2J(C,H) values reflect the stereochemistry for glycol connectivity. Based on the observed 2J(C,H) values for galactose, glucose, and mannose, 2J(C,H) profiles for other aldohexopyranoses are proposed. A combination of 2J(C,H) values was found to be useful for identification of aldohexopyranosyl residues in glycans. [structure: see text]
MeSH term(s)	Aldehydes ; Galactose/chemistry ; Glucose/analogs & derivatives ; Glucose/chemical synthesis ; Glucose/chemistry ; Hexoses/chemical synthesis ; Hexoses/chemistry ; Lactose/chemistry ; Magnetic Resonance Spectroscopy/methods ; Mannose/chemistry ; Models, Molecular ; Sucrose/chemistry
Chemical Substances	Aldehydes ; Hexoses ; Sucrose (57-50-1) ; Glucose (IY9XDZ35W2) ; Lactose (J2B2A4N98G) ; Mannose (PHA4727WTP) ; Galactose (X2RN3Q8DNE)
Language	English
Publishing date	2005-02-17
Publishing country	United States
Document type	Journal Article
ISSN	1523-7060
ISSN	1523-7060
DOI	10.1021/ol047358a
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Article: A practical synthesis of the phytosiderophore 2'-deoxymugineic acid: a key to the mechanistic study of iron acquisition by graminaceous plants.

Namba, Kosuke / Murata, Yoshiko / Horikawa, Manabu / Iwashita, Takashi / Kusumoto, Shoichi

Angewandte Chemie (International ed. in English)

2007 Volume 46, Issue 37, Page(s) 7060–7063

MeSH term(s)	Animals ; Azetidinecarboxylic Acid/analogs & derivatives ; Azetidinecarboxylic Acid/chemistry ; Azetidinecarboxylic Acid/metabolism ; Iron/metabolism ; Membrane Transport Proteins/genetics ; Membrane Transport Proteins/metabolism ; Molecular Structure ; Oocytes/cytology ; Oocytes/physiology ; Patch-Clamp Techniques ; Plant Proteins/genetics ; Plant Proteins/metabolism ; Plants/chemistry ; Poaceae/chemistry ; Siderophores/chemical synthesis ; Siderophores/chemistry ; Siderophores/metabolism ; Xenopus laevis
Chemical Substances	Membrane Transport Proteins ; Plant Proteins ; Siderophores ; Azetidinecarboxylic Acid (2517-04-6) ; Iron (E1UOL152H7) ; mugineic acid (KR256JY76I)
Language	English
Publishing date	2007
Publishing country	Germany
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	2011836-3
ISSN	1521-3773 ; 1433-7851
ISSN (online)	1521-3773
ISSN	1433-7851
DOI	10.1002/anie.200702403
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Article ; Online: Synthesis and biological activity of phosphoglycolipids from Thermus thermophilus.

Fujimoto, Yukari / Mitsunobe, Kunihiro / Fujiwara, Satoko / Mori, Motoko / Hashimoto, Masahiro / Suda, Yasuo / Kusumoto, Shoichi / Fukase, Koichi

Organic & biomolecular chemistry

2013 Volume 11, Issue 30, Page(s) 5034–5041

Abstract: An extreme thermophile, Thermus thermophilus, has very unique glycolipids on the cell surface. The acidic immunostimulatory phosphoglycolipid of T. thermophilus was synthesized for the first time, with newly developed glycosylation methods using 3- ... ...

Abstract	An extreme thermophile, Thermus thermophilus, has very unique glycolipids on the cell surface. The acidic immunostimulatory phosphoglycolipid of T. thermophilus was synthesized for the first time, with newly developed glycosylation methods using 3-nitropyridyl (3NPy) and 4,6-dimethoxy-1,3,5-triazin-2-yl (DMT) glycosides as glycosyl donors. The analogues of the phosphoglycolipid, which include a diastereomer possessing the opposite configuration at the diacyl glycerol moiety, were also synthesized. The biological activities of the synthesized compounds were elucidated with cytokine inductions (IL-6 and TNF-α). A synthetic phosphoglycolipid with a natural-type diacyl glycerol configuration showed apparent immunostimulatory activity, whereas its diastereomer did not. The present study revealed that the configuration at the diacyl glycerol moiety of the phosphoglycolipids is important for immunostimulation, suggesting the existence of the particular receptor/recognizing protein that can recognize the stereochemistry of the glycerol part.
MeSH term(s)	Dose-Response Relationship, Drug ; Glycolipids/chemical synthesis ; Glycolipids/isolation & purification ; Glycolipids/pharmacology ; Humans ; Interleukin-6/biosynthesis ; Interleukin-6/blood ; Interleukin-6/immunology ; Molecular Structure ; Thermus thermophilus/chemistry ; Tumor Necrosis Factor-alpha/biosynthesis ; Tumor Necrosis Factor-alpha/blood ; Tumor Necrosis Factor-alpha/immunology
Chemical Substances	Glycolipids ; Interleukin-6 ; Tumor Necrosis Factor-alpha
Language	English
Publishing date	2013-08-14
Publishing country	England
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	2097583-1
ISSN	1477-0539 ; 1477-0520
ISSN (online)	1477-0539
ISSN	1477-0520
DOI	10.1039/c3ob40899j
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