英: protoheme

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2017/03/03 21:14:13」(JST)

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Heme B or haem B (also known as protoheme IX) is the most abundant heme. Hemoglobin and myoglobin are examples of oxygen transport proteins that contain heme B. The peroxidase family of enzymes also contain heme B. The COX-1 and COX-2 enzymes (cyclooxygenase) of recent fame, also contain heme B at one of two active sites.

Generally, heme B is attached to the surrounding protein matrix (known as the apoprotein) through a single coordination bond between the heme iron and an amino-acid side-chain.

Both hemoglobin and myoglobin have a coordination bond to an evolutionarily-conserved histidine, while nitric oxide synthase and cytochrome P450 have a coordination bond to an evolutionarily-conserved cysteine bound to the iron center of heme B.

Since the iron in heme B containing proteins is bound to the four nitrogens of the porphyrin (forming a plane) and a single electron donating atom of the protein, the iron is often in a pentacoordinate state. When oxygen or the toxic carbon monoxide is bound the iron becomes hexacoordinated. The correct structures of heme B and heme S were first elucidated by German chemist Hans Fischer.^[1]

References

^ Fischer, H.; Orth, H. (1934). Die Chemie des Pyrrols. Liepzig: Akademische Verlagsgesellschaft.

English Journal

Thermophilic bacteria are potential sources of novel Rieske non-heme iron oxygenases.

Chakraborty J1, Suzuki-Minakuchi C1, Okada K1, Nojiri H2.
AMB Express.AMB Express.2017 Dec;7(1):17. doi: 10.1186/s13568-016-0318-5. Epub 2017 Jan 4.
Rieske non-heme iron oxygenases, which have a Rieske-type [2Fe-2S] cluster and a non-heme catalytic iron center, are an important family of oxidoreductases involved mainly in regio- and stereoselective transformation of a wide array of aromatic hydrocarbons. Though present in all domains of life, th
PMID 28050858

Mesenchymal stem cells: a future experimental exploration for recession of diabetic nephropathy.

Hamza AH1,2, Al-Bishri WM1, Damiati LA3, Ahmed HH4.
Renal failure.Ren Fail.2017 Nov;39(1):67-76. doi: 10.1080/0886022X.2016.1244080. Epub 2016 Oct 23.
BACKGROUND: The progresses made in stem cell therapy offer an innovative approach and exhibit great potential for the repair of damaged organs and tissues. This study was conducted with a view to find the mechanisms responsible for the effectiveness of bone marrow-derived mesenchymal stem cells (BM-
PMID 27774826

Fractionation, enzyme inhibitory and cellular antioxidant activity of bioactives from purple sweet potato (Ipomoea batatas).

Esatbeyoglu T1, Rodríguez-Werner M2, Schlösser A3, Winterhalter P2, Rimbach G3.
Food chemistry.Food Chem.2017 Apr 15;221:447-456. doi: 10.1016/j.foodchem.2016.10.077. Epub 2016 Oct 19.
Sweet potato (Ipomoea batatas L.) is mainly cultivated in Asia. The deep purple color of purple sweet potato (PSP) is due to the high content of acylated anthocyanins. In the present study, PSP-derived polyphenols were identified using HPLC-PDA and HPLC-ESI-MSn analyses. After concentration of the p
PMID 27979226

Japanese Journal

ヤツメウナギの祖先型ヘモグロビンNode25タンパク質の合成および機能解析

幕晋一,MAKU Shinichi
法政大学大学院紀要（理工学・工学研究科編） (55), 2014-03-24
… UV-visible spectra showed that this purified Node25 protein holds protoheme group. …
NAID 120005524565

Assimilation of Metal Ions Bound to Porphyrins or Porphyrin-Peptides by Vibrio vulnificus, a Human Pathogen Inhabiting Estuarine and Marine Environments

MIYOSHI SHIN-ICHI,SASAKI TOMOKO,KAKU NAHOKO,INOUE TAKAHARU,UOZUMI NATSUKI,MAEHARA YOKO,NAKAO HIROSHI
Biocontrol science 15(1), 1-6, 2010-03-10
… In addition to protoheme, this species can utilize Fe-TCPP [ferric tetrakis (4-carboxyphenyl) porphine] as an iron source. …
NAID 10027043950

Electronic Properties and Thermal Stability of Soluble Redox Proteins from a Thermophilic Purple Sulfur Photosynthetic Bacterium, Thermochromatium tepidum

Kobayashi Masayuki,Saito Takayuki,Takahashi Kiyomichi,Wang Zheng-Yu,Nozawa Tsunenori
Bulletin of the Chemical Society of Japan 78(12), 2164-2170, 2005
… Cytochrome <I>c</I>' has a high-spin protoheme with a redox midpoint potential of +100 mV at pH 7, similar to those of many other photosynthetic bacteria. …
NAID 130004151838

Related Pictures

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★リンクテーブル★

リンク元	「ヘム」「プロトヘム」

「ヘム」

Heme B
Names
	Other names Iron protoporphyrin IX,; protoheme IX
Identifiers
CAS Number	14875-96-8
3D model (Jmol)	Interactive image
ChemSpider	16739950
ECHA InfoCard	100.114.904
MeSH	Heme+b
PubChem	444098
	InChI InChI=1S/C34H34N4O4.Fe/c1-7-21-17(3)25-13-26-19(5)23(9-11-33(39)40)31(37-26)16-32-24(10-12-34(41)42)20(6)28(38-32)15-30-22(8-2)18(4)27(36-30)14-29(21)35-25;/h7-8,13-16H,1-2,9-12H2,3-6H3,(H4,35,36,37,38,39,40,41,42);/q;+2/p-2/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-; Key: KABFMIBPWCXCRK-RGGAHWMASA-L ; InChI=1/C34H34N4O4.Fe/c1-7-21-17(3)25-13-26-19(5)23(9-11-33(39)40)31(37-26)16-32-24(10-12-34(41)42)20(6)28(38-32)15-30-22(8-2)18(4)27(36-30)14-29(21)35-25;/h7-8,13-16H,1-2,9-12H2,3-6H3,(H4,35,36,37,38,39,40,41,42);/q;+2/p-2/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-;/rC34H32FeN4O4/c1-7-21-17(3)25-13-29-20(6)24(10-12-34(42)43)32-16-28-23(9-11-33(40)41)18(4)26(37-28)14-31-22(8-2)19(5)30(15-27(21)36-25)38(31)35-39(29)32/h7-8,13-16H,1-2,9-12H2,3-6H3,(H,40,41)(H,42,43)/b25-13-,26-14-,27-15-,28-16-,29-13-,30-15-,31-14-,32-16- Key: KABFMIBPWCXCRK-SMDPYJEOBB ;
	SMILES OC(=O)CC/C6=C(\C)/C=3/N=C6/C=C2/C(/CCC(O)=O)=C(/C)\C1=C\C5=N\C(=C/c4n([Fe]N12)c(C=3)c(C=C)c4C)C(\C=C)=C5\C ;
Properties
Chemical formula	C34H32O4N4Fe
Molar mass	616.487
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

　　[★]

英: heme
同: プロトヘム protoheme、フェロプロトポルフィリンIX ferroprotoporphyrin IX
関: ヘマチン hematin

ポルフィリンと鉄イオンの錯体

生合成

→ポルフィリン

反応場所						酵素	補酵素	酵素阻害物質	酵素の障害による疾患
ミトコンドリア	サクシニルCoA succinyl-CoA	グリシン glycine	5-アミノレブリン酸 aminolevulinic acid aminolevulinate ALA	CoA	CO2	5-アミノレブリン酸シンターゼ ALA synthase	ビタミンB6
細胞質	5-アミノレブリン酸 aminolevulinic acid aminolevulinate ALA	←2分子	ポルホビリノゲン porphobilinogen PBG	2H2O		ALA dehydratase		Pb
細胞質	ポルホビリノゲン porphobilinogen PBG		ヒドロキシメチルビラン	4NH3		ウロポルフィリゲノンIシンターゼ uroporphyrinogen I synthase			急性間欠性ポルフィリン症 acute intermittent porphyria
細胞質	ヒドロキシメチルビラン		ウロポルフィリノゲンIII			ウロポルフィリゲノンIIIシンターゼ uroporphyrinogen III synthase
細胞質	ウロポルフィリノゲンIII		コプロポルフィリノゲンIII	4CO2		ウロポルフィリノゲンデカルボキシラーゼ			晩発性皮膚ポルフィリン症 porphyria cutanea tarda
ミトコンドリア	コプロポルフィリノゲンIII		プロトポルフィリノゲンIX	2CO2		コプロポルフィリノゲンオキシダーゼ
ミトコンドリア	プロトポルフィリノゲンIX		プロトポルフィリンIX			プロトポルフィリノゲンオキシダーゼ
ミトコンドリア	プロトポルフィリンIX	Fe2+	ヘム			フェロケラターゼ		Pb

生合成の場所

哺乳類細胞では、赤血球以外は何処でも行われる(ミトコンドリアを有するなら)
実際には、赤血球前駆細胞(erythroid precursor cell)で85%行われており、残りは肝細胞で行われている。

「プロトヘム」

　　[★]

英: protoheme
関: ヘム

[1] Fischer, H.; Orth, H. (1934). Die Chemie des Pyrrols. Liepzig: Akademische Verlagsgesellschaft.

匿名

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案内

案内

protoheme