lipoamide

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/09/13 12:45:40」(JST)

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Lipoamide

Names
IUPAC name 5-(1,2-Dithiolan-3-yl)pentanamide
Identifiers
CAS Number	940-69-2 Y
ChEBI	CHEBI:17460 N
ChemSpider	5360246 Y
Jmol 3D model	Interactive image
MeSH	lipoamide
PubChem	6992093
InChI InChI=1S/C8H15NOS2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H2,9,10)/t7-/m1/s1 Y Key: FCCDDURTIIUXBY-SSDOTTSWSA-N Y InChI=1/C8H15NOS2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H2,9,10)/t7-/m1/s1 Key: FCCDDURTIIUXBY-SSDOTTSWBG
SMILES O=C(N)CCCC[C@H]1SSCC1
Properties
Chemical formula	C8H15NOS2
Molar mass	205.343 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Lipoamide is a trivial name for 6,8-dithiooctanoic amide. It is 6,8-dithiooctanoic acid's functional form where the carboxyl group is attached to protein (or any other amine) by an amide linkage (containing -NH₂). Sometimes lipoamide is used to refer to protein bound lipoic acid, but this can be misleading as this is technically incorrect. Lipoyl-protein or lipoyl-domain are better terms to refer to protein bound lipoic acid.

There are no reported occurrences of free lipoamide in nature.

See also

• Lipoic acid

UpToDate Contents

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• Determination of glutaredoxin enzyme activity and protein S-glutathionylation using fluorescent eosin-glutathione.

• Coppo L1, Montano SJ2, Padilla AC3, Holmgren A4.
• Analytical biochemistry.Anal Biochem.2016 Apr 15;499:24-33. doi: 10.1016/j.ab.2016.01.012. Epub 2016 Jan 31.
• Glutaredoxins catalyze glutathione-dependent disulfide oxidoreductions, particularly reduction of glutathione (GSH)-protein mixed disulfides. Mammalian glutaredoxins are present in the cytosol/nucleus as Grx1 or in mitochondria as Grx2a. Here we describe di-eosin-glutathione disulfide (Di-E-GSSG) as
• PMID 26836485

• Roles of Fe-S proteins: from cofactor synthesis to iron homeostasis to protein synthesis.

• Pain D1, Dancis A2.
• Current opinion in genetics & development.Curr Opin Genet Dev.2016 Apr 7;38:45-51. doi: 10.1016/j.gde.2016.03.006. [Epub ahead of print]
• Fe-S cluster assembly is an essential process for all cells. Impairment of Fe-S cluster assembly creates diseases in diverse and surprising ways. In one scenario, the loss of function of lipoic acid synthase, an enzyme with Fe-S cluster cofactor in mitochondria, impairs activity of various lipoamide
• PMID 27061491

• Global Kinetic Analysis of Mammalian E3 Reveals pH-dependent NAD+/NADH Regulation, Physiological Kinetic Reversibility, and Catalytic Optimum.

• Moxley MA1, Beard DA2, Bazil JN1.
• The Journal of biological chemistry.J Biol Chem.2016 Feb 5;291(6):2712-30. doi: 10.1074/jbc.M115.676619. Epub 2015 Dec 7.
• Mammalian E3 is an essential mitochondrial enzyme responsible for catalyzing the terminal reaction in the oxidative catabolism of several metabolites. E3 is a key regulator of metabolic fuel selection as a component of the pyruvate dehydrogenase complex (PDHc). E3 regulates PDHc activity by altering
• PMID 26644471

Japanese Journal

• Ginsenoside Rh1 Eliminates the Cytoprotective Phenotype of Human Immunodeficiency Virus Type 1-Transduced Human Macrophages by Inhibiting the Phosphorylation of Pyruvate Dehydrogenase Lipoamide Kinase Isozyme 1

• Jeong Jin-Ju,Kim Baek,Kim Dong-Hyun
• Biological and Pharmaceutical Bulletin 36(7), 1088-1094, 2013
• … Furthermore, ginsenoside Rh1 inhibited pyruvate dehydrogenase lipoamide kinase isozyme 1 (PDK-1) phosphorylation. …
• NAID 130003361469

• Gene cloning and characterization of dihydrolipoamide dehydrogenase from Microbacterium luteolum : A useful enzymatic regeneration system of NAD^+ from NADH(ENZYMOLOGY, PROTEIN ENGINEERING, AND ENZYME TECHNOLOGY)

• Kurokawa Junji,Asano Manabu,Nomoto Shunsuke [他],Makino Yoshihide,Itoh Nobuya
• Journal of bioscience and bioengineering 109(3), 218-223, 2010-03
• … luteolum (MluLPD) accepted not only lipoamide but also some artificial electron acceptors such as dichlorophenolindophenol (DCIP) and nitrotetrazolium blue (NTB), that is, it functions as a diaphorase. …
• NAID 110007612425

• Production of L-malic acid with fixation of HCO^-_3 by malic enzyme-catalyzed reaction based on regeneration of coenzyme on electrode modified by layer-by-layer self-assembly method(ENZYMOLOGY, PROTEIN ENGINEERING, AND ENZYME TECHNOLOGY)

• Zheng Haitao,Ohno Yoko,Nakamori Toshihiko [他],Suye Shin-ichiro
• Journal of bioscience and bioengineering 107(1), 16-20, 2009-01
• … The L-malic acid production was based on electrochemical regeneration of NADH on a carbon plate electrode modified by layer-by-layer adsorption of polymer-bound mediator (Alginic acid bound viologen derivative, Alg-V), polymer-bound coenzyme (Alginic acid bound NAD^+, Alg-NAD^+), and lipoamide dehydrogenase (LipDH). …
• NAID 110007042027

Related Links

• Lipoamide | definition of lipoamide by Medical dictionary

li·po·ic ac·id (li-pō'ik as'id), A bacterial growth factor present in yeast and liver extracts; may be useful in the treatment of mushroom poisoning. Functions as the amide (lipoamide) cofactor in the disulfide (-S-S-) form in the transfer of ...

• Lipoamide - definition of Lipoamide by The Free Dictionary

li·po·ic acid (lĭ-pō′ĭk) n. An organic acid, C 8 H 14 S 2 O 2, that is essential for decarboxylation of pyruvate to acetyl coenzyme A during aerobic metabolism. ... The result was supported by Reed (1973), who thought that lipoamide ...

Related Pictures

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★リンクテーブル★

拡張検索	「dihydrolipoamide acetyltransferase」「dihydrolipoamide dehydrogenase」「dihydrolipoamide」

「dihydrolipoamide acetyltransferase」

　　[★]

ジヒドロリ・アミドアセチルトランスフェラーゼ

関

dihydrolipoyl acetyltransferase、dihydrolipoyllysine-residue acetyltransferase

「dihydrolipoamide dehydrogenase」

　　[★]

ジヒドロリ・アミドデヒドロゲナーゼ、ジヒドロリ・アミド脱水素酵素

関

diaphorase

「dihydrolipoamide」

　　[★] ジヒドロリポアミド