関: D-mannose

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/07/08 20:12:54」(JST)

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Mannose is a sugar monomer of the aldohexose series of carbohydrates. Mannose is a C-2 epimer of glucose. Mannose is important in human metabolism, especially in the glycosylation of certain proteins. Several congenital disorders of glycosylation are associated with mutations in enzymes involved in mannose metabolism.^[1]

Structure

Mannose commonly exists as two different sized rings, the pyranose (six-membered) form and the furanose (five-membered) form. Each ring closure can have either an alpha or beta configuration at the anomeric position. The chemical rapidly undergoes isomerization among these four forms.

D-Mannose isomers (Haworth projections)
Percent composition
α-D-Mannofuranose <1 %	β-D-Mannofuranose <1 %
α-D-Mannopyranose 67 %	β-D-Mannopyranose 33 %

Metabolism

Metabolism of common monosaccharides and related reactions

While much of the mannose used in glycosylation is believed to be derived from glucose, in cultured hepatoma (cancerous cells from the liver) cells, most of the mannose for glycoprotein biosynthesis comes from extracellular mannose, not glucose.^[2] Many of the glycoproteins produced in the liver are secreted into the bloodstream, so dietary mannose is distributed throughout the body. ^[3]

Mannose is present in numerous glycoconjugates including N-linked glycosylation of proteins. C-mannosylation is also abundant and can be found in collagen-like regions.

The digestion of many polysaccharides and glycoproteins yields mannose which is phosphorylated by hexokinase to generate mannose-6-phosphate. Mannose-6-phosphate is converted to fructose-6-phosphate, by the enzyme phosphomannose isomerase, and then enters the glycolytic pathway or is converted to glucose-6-phosphate by the gluconeogenic pathway of hepatocytes.

Biotechnology

Recombinant proteins produced in yeast may be subject to mannose addition in patterns different from those used by mammalian cells.^[4] This difference in recombinant proteins from those normally produced in mammalian organisms may influence the effectiveness of vaccines.

Formation

Mannose can be formed by the oxidation of mannitol.

It can also be formed from glucose in the Lobry-de Bruyn-van Ekenstein transformation.

Etymology

The root of both "mannose" and "mannitol" is manna, which the Bible records as the food supplied to the Israelites during their journey in the region of Sinai. Several trees and shrubs can produce a substance called manna, such as the "manna tree" (Fraxinus ornus) from whose secretions mannitol was originally isolated.

Configuration

Mannose differs from glucose by inversion of the C-2 chiral center. Mannose displays a pucker in the solution ring form.

This apparently simple change leads to the drastically different biochemistry of the two hexoses, as it does the remaining six aldohexoses.

Mannose PTS Permease

Mannose XYZ permease Complex Diagram: Entry of PEP which donates a high energy phosphate that gets passed through the transporter system and eventually assist in the entry of mannose (in this example otherwise it would any hexose sugar) and results in the formation of mannose-6-phosphate.

Video illustration of the MANXYZ sugar transporter complex transferring the high energy phosphate for PEP to the other subunits of the complex

The PEP-dependent sugar transporting phosphotransferase system transports and simultaneously phosphorylates its sugar substrates. Mannose XYZ permease is a member of the family, with this distinct method being used by bacteria for sugar uptake particularly exogenous hexoses in the case of Mannose XYZ in order to release the phosphate esters into the cell cytoplasm in preparation for metabolism primarily through the route of glycolysis.^[5] The MANXYZ transporter complex is also involved in infection of E. Coli by bacteriophage Lambda, with subunit ManX and ManY being sufficient for proper Lambda phage infection.^[6] MANXYZ possesses four domains in three polypeptide chains; ManX, ManY, and ManZ. The ManX subunit forms a homodimer that is localized to the cytoplasmic side of the membrane. ManX contains two domains IIA and IIB linked by a hinge peptide with each domain containing a phosphorylation site and phosphoryl transfer occurs between both subunits.^[7] ManX can be membrane bound or non-membrane bound.^[6] The MANY and MANZ subunits are hydrophobic integral membrane proteins with six and one transmembrane alpha helical spanner(s).^[8] The phosphoryl group of PEP is transferred to the imported sugar via E1 (Enzyme 1), HPr (Histidine Protein) phosphate carrier and then to the MANX, MANY, and MANZ subunits of the MANXYZ transportation complex which phosphorylate the entering hexose sugar creating a hexose-6-phosphate.

References

^ Freeze, H. H.; Sharma, V. (2010). "Metabolic manipulation of glycosylation disorders in humans and animal models". Seminars in Cell & Developmental Biology 21 (6): 655–662. doi:10.1016/j.semcdb.2010.03.011. PMC 2917643. PMID 20363348. edit
^ Alton, G.; Hasilik, M.; Niehues, R.; Panneerselvam, K.; Etchison, J. R.; Fana, F.; Freeze, H. H. (1998). "Direct utilization of mannose for mammalian glycoprotein biosynthesis". Glycobiology 8 (3): 285–295. doi:10.1093/glycob/8.3.285. PMID 9451038. edit
^ Davis, J. A.; Freeze, H. H. (2001). "Studies of mannose metabolism and effects of long-term mannose ingestion in the mouse". Biochimica et biophysica acta 1528 (2–3): 116–126. doi:10.1016/S0304-4165(01)00183-0. PMID 11687298. edit
^ Vlahopoulos, S.; Gritzapis, A. D.; Perez, S. A.; Cacoullos, N.; Papamichail, M.; Baxevanis, C. N. (2009). "Mannose addition by yeast Pichia Pastoris on recombinant HER-2 protein inhibits recognition by the monoclonal antibody herceptin". Vaccine 27 (34): 4704–4708. doi:10.1016/j.vaccine.2009.05.063. PMID 19520203. edit
^ Postma, P. W.; Lengeler, J. W.; Jacobson, G. R. (1993). "Phosphoenolpyruvate:carbohydrate phosphotransferase systems of bacteria". Microbiological reviews 57 (3): 543–594. PMC 372926. PMID 8246840. edit
^ ^a ^b Erni, B.; Zanolari, B. (1985). "The mannose-permease of the bacterial phosphotransferase system. Gene cloning and purification of the enzyme IIMan/IIIMan complex of Escherichia coli". The Journal of biological chemistry 260 (29): 15495–15503. PMID 2999119. edit
^ Erni, B.; Zanolari, B.; Graff, P.; Kocher, H. P. (1989). "Mannose permease of Escherichia coli. Domain structure and function of the phosphorylating subunit". The Journal of biological chemistry 264 (31): 18733–18741. PMID 2681202. edit
^ Huber, F.; Erni, B. (1996). "Membrane topology of the mannose transporter of Escherichia coli K12". European journal of biochemistry / FEBS 239 (3): 810–817. doi:10.1111/j.1432-1033.1996.0810u.x. PMID 8774730. edit

UpToDate Contents

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1. 女性における再発性尿路感染症 recurrent urinary tract infection in women
2. マンノース結合レクチン欠損症 mannose binding lectin deficiency
3. 感染症を繰り返す成人に対するアプローチ approach to the adult with recurrent infections
4. マンノース結合レクチン mannose binding lectin
5. 自然免疫系の概要 an overview of the innate immune system

English Journal

Physicochemical characterization and toxicological evaluation of plant-based anionic polymers and their nanoparticulated system for ocular delivery.

Pathak D1, Kumar P, Kuppusamy G, Gupta A, Kamble B, Wadhwani A.
Nanotoxicology.Nanotoxicology.2014 Dec;8(8):843-55. doi: 10.3109/17435390.2013.834996. Epub 2013 Sep 18.
The water-soluble fractions of mucilages and gum from the seeds of fenugreek, isphagula and mango bark exudate were isolated, purified and characterized using X-ray diffraction (XRD) spectrometry, Fourier transform infrared spectroscopy (FT-IR), maldi/GC-MS, elemental analysis, 1D ((1)H and (13)C) a
PMID 23952497

High-level coproduction, purification and characterisation of laccase and exopolysaccharides by Coriolus versicolor.

Que Y1, Sun S2, Xu L3, Zhang Y4, Zhu H5.
Food chemistry.Food Chem.2014 Sep 15;159:208-13. doi: 10.1016/j.foodchem.2014.03.063. Epub 2014 Mar 20.
In this study, a two-stage pH-shift fermentation process was developed for the coproduction of laccase and exopolysaccharides (EPS) by Coriolus versicolor. At the same time, laccase and EPS were purified and characterised in detail. The results showed that the highest laccase and EPS production reac
PMID 24767046

Influence of the structural features of commercial mannoproteins in white wine protein stabilization and chemical and sensory properties.

Ribeiro T1, Fernandes C2, Nunes FM3, Filipe-Ribeiro L4, Cosme F5.
Food chemistry.Food Chem.2014 Sep 15;159:47-54. doi: 10.1016/j.foodchem.2014.02.149. Epub 2014 Mar 12.
The cloudy aspect formed in white wines due to protein instability is a visual defect. Sodium bentonite is the most commonly used fining agent to treat this instability, but has usually a negative impact on the wine's physicochemical and sensory characteristics. Aiming to find suitable alternatives,
PMID 24767025

Japanese Journal

アスコルビン酸代謝を介した活性酸素種の生理活性調節

丸田隆典
ビタミン 88(1), 1-10, 2014-01-25
… Biochemical and molecular genetic approaches we have found by that AsA is mainly synthesized via a D-mannose/L-galactose pathway and that the pathway is regulated by light/dark and plastid-derived signals. …
NAID 110009767425

Characterization of Mannose Isomerase from a Cellulolytic Actinobacteria Thermobifida fusca MBL10003

Kasumi Takafumi,Mori Sumiko,Kaneko Satoshi [他]
Journal of applied glycoscience 61(1), 21-25, 2014
NAID 40019983556

Free and Bound Volatile Compounds in Juice and Peel of Eureka Lemon

Zhong Siqiong,Ren Jingnan,Chen Dewen,Pan Siyi,Wang Kexing,Yang Shuzhen,Fan Gang
Food Science and Technology Research 20(1), 167-174, 2014
… Mannose and glucose were found as sugar moiety in juice, and glucose was found the only sugar linked to bound volatiles in peel. …
NAID 130003392434

Related Pictures

★リンクテーブル★

リンク元	「補体」「マンノース」
拡張検索	「mannose 6-phosphate receptor」「mannose-binding protein-associated serine protease」「mannose-binding protein」「mannose binding protein」「D-mannose」

「補体」

Mannose
	; D-Mannopyranose
	; Fischer projections
Identifiers
CAS number	31103-86-3
PubChem	18950
ChemSpider	17893 D-mannopyranose
UNII	PHA4727WTP
MeSH	Mannose
ChEMBL	CHEMBL469448
Properties
Molecular formula	C6H12O6
Molar mass	180.16 g mol−1
	Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
	(verify) (what is: /?)
	Infobox references

　　[★]

英: complement
同: アレキシン alexin
関: 補体活性化経路、補体価

図：IMM.63

pathway	start	first step
classical pathway	antigen-antibody complex	C1q, C1r, C1s, C4, C2
lectin pathway	mannose-binding lectin or ficolin binds carbohydrate on pathogen surface	MBL/ficolin, MASP-2, C4, C2
alternative pathway	pathogen surface	C3, B, D

補体の相互作用 IMM.62

古典的経路 classical pathway

C1qがカスケードの最初となる。3つの方法で補体カスケードがはじまる。

(1)多価陰イオン表面(例えば、グラム陰性細菌のリポテイコ酸)
(2)バクテリアの多糖のホスホコリンに結合(例えば肺炎球菌のC蛋白質)
(3)抗原抗体複合体に結合して自然免疫と獲得免疫のエフェクター機構を結びつける。

レクチン経路 lectin pathway

炭化水素鎖を認識するレクチンがカスケードの最初となる。

1. lectin MBL：mannose-containing carbohydrates
2. ficolin　：N-acetylglucosamine

代替経路 alternative pathway

C3からはじまる。血漿中のC3が病原体の表面で自発的に活性化されることで補体反応がはじまる。

３つの経路は共通してC3 convertaseを生成。C3 convertaseはC3→C3a+C3b
C3a: C3a is a peptide mediator of local inflammation
C3b: C3b binds covalently to the bacterial cell membrane and opsonizes the bacteria

C5 convertaseはC3bにC3 convertaseが結合してできる
C5 converaseはC5→C5a+C5b
C5a: powerful peptide mediator of inflammation
C5b: C5b,C6,C7,C8,C9: membrane-attack complex

C3aとC5a。C4a

炎症部位に血管外に抗体、補体、食細胞を集め、組織液を増やすことで抗原提示細胞がリンパ節に移動するのを促進する(IMM.75)

C5a,C3a,C4a: smooth muscle contraction.(IMM.75)
C5a,C3a: act on the endo thelial cells lining blood vessels to induce adhesion molecules.(IMM.75)
C5a>C3a>C4a: increase in blood flow, increase vascular permeability, increase binding of phagocytes to exdothielial cells.(IMM.76)
C5a: activates mast cells to release mediators, such as histamine and TNF-α. that contribute the inflammatory response(IMM.76).
C5a: acts directly on neutrophils and monocytes and attracting neutrophils and monocytes(IMM.75)
C3a: contributes to the pypotension and edema seen in endotoxic shock
C5a: activated by endotoxin, funcions in neutrophil chemotaxis

C5a

臨床関連

増加：

関節リウマチ、ウェゲナー肉芽腫、リウマチ熱、ベーチェット病

減少：低補体血症

全身性エリテマトーデス、悪性関節リウマチ、急性糸球体腎炎、膜性増殖性糸球体腎炎、結節性多発動脈炎, polyarteritis nodosa, PN

「マンノース」

　　[★]

英: mannose Man
同: セミノース seminose、カルビノース carubinose
関

「mannose 6-phosphate receptor」

　　[★]

マンノース6リン酸受容体、マンノース6リン酸レセプター

関: IGF type 2 receptor、IGF-2 receptor、IGF-II receptor、insulin-like growth factor II receptor、MPR

「mannose-binding protein-associated serine protease」

　　[★]

マンノース結合タンパク質関連セリンプロテアーゼ

関: MASP、MBP-associated serine protease

「mannose-binding protein」

　　[★]

マンノース結合タンパク質

関: mannose-binding lectin

「mannose binding protein」

　　[★] マンノース結合タンパク質

「D-mannose」

　　[★]

D-マンノース

関: mannose

[1] Freeze, H. H.; Sharma, V. (2010). "Metabolic manipulation of glycosylation disorders in humans and animal models". Seminars in Cell & Developmental Biology 21 (6): 655–662. doi:10.1016/j.semcdb.2010.03.011. PMC 2917643. PMID 20363348. edit

[2] Alton, G.; Hasilik, M.; Niehues, R.; Panneerselvam, K.; Etchison, J. R.; Fana, F.; Freeze, H. H. (1998). "Direct utilization of mannose for mammalian glycoprotein biosynthesis". Glycobiology 8 (3): 285–295. doi:10.1093/glycob/8.3.285. PMID 9451038. edit

[3] Davis, J. A.; Freeze, H. H. (2001). "Studies of mannose metabolism and effects of long-term mannose ingestion in the mouse". Biochimica et biophysica acta 1528 (2–3): 116–126. doi:10.1016/S0304-4165(01)00183-0. PMID 11687298. edit

[4] Vlahopoulos, S.; Gritzapis, A. D.; Perez, S. A.; Cacoullos, N.; Papamichail, M.; Baxevanis, C. N. (2009). "Mannose addition by yeast Pichia Pastoris on recombinant HER-2 protein inhibits recognition by the monoclonal antibody herceptin". Vaccine 27 (34): 4704–4708. doi:10.1016/j.vaccine.2009.05.063. PMID 19520203. edit

[Postma_1993-5] Postma, P. W.; Lengeler, J. W.; Jacobson, G. R. (1993). "Phosphoenolpyruvate:carbohydrate phosphotransferase systems of bacteria". Microbiological reviews 57 (3): 543–594. PMC 372926. PMID 8246840. edit

[Erni_1985-6] Erni, B.; Zanolari, B. (1985). "The mannose-permease of the bacterial phosphotransferase system. Gene cloning and purification of the enzyme IIMan/IIIMan complex of Escherichia coli". The Journal of biological chemistry 260 (29): 15495–15503. PMID 2999119. edit

[Erni_1989-7] Erni, B.; Zanolari, B.; Graff, P.; Kocher, H. P. (1989). "Mannose permease of Escherichia coli. Domain structure and function of the phosphorylating subunit". The Journal of biological chemistry 264 (31): 18733–18741. PMID 2681202. edit

[Huber_1996-8] Huber, F.; Erni, B. (1996). "Membrane topology of the mannose transporter of Escherichia coli K12". European journal of biochemistry / FEBS 239 (3): 810–817. doi:10.1111/j.1432-1033.1996.0810u.x. PMID 8774730. edit

匿名

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案内

案内

mannose