N'-Formylkynurenine: Difference between revisions

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	{{DISPLAYTITLE:''N'''-Formylkynurenine}}		{{DISPLAYTITLE:''N'''-Formylkynurenine}}
	{{chembox		{{chembox
			\| Watchedfields = changed
	\| verifiedrevid = ~~392264679~~		\| verifiedrevid = 437363582
	\|Name=''N′''-Formylkynurenine		\| Name=''{{prime\|N}}''-Formylkynurenine
⚫	\|~~ImageFile~~=N-formylkynurenine~~.svg~~
			\| ImageFile=N-formyl-L-kynurenine.svg
	\|ImageSize=		\| ImageSize=
	\|IUPACName=
			\| SystematicName=(2''S'')-2-Amino-4-(2-formamidophenyl)-4-oxobutanoic acid
	\|OtherNames=
			\| OtherNames=''{{prime\|N}}''-Formyl-<small>L</small>-kynurenine
	\|Section1= {{Chembox Identifiers		\|Section1={{Chembox Identifiers
⚫	\| CASNo=~~1022~~-31-7
			\| CASNo_Ref = {{cascite\|correct\|??}}
⚫	\| PubChem=~~910~~
		⚫	\| CASNo=3978-11-8
	\| SMILES=
			\| ChEBI = 30249
	\| MeSHName=N'-formylkynurenine
			\| ChEMBL = 3577708
			\| ChemSpiderID = 388843
			\| KEGG = C02700
		⚫	\| PubChem=439788
			\| UNII=PS20W0733S
			\| StdInChI=1S/C11H12N2O4/c12-8(11(16)17)5-10(15)7-3-1-2-4-9(7)13-6-14/h1-4,6,8H,5,12H2,(H,13,14)(H,16,17)/t8-/m0/s1
			\| StdInChIKey = BYHJHXPTQMMKCA-QMMMGPOBSA-N
			\| SMILES=C1=CC=C(C(=C1)C(=O)C(C(=O)O)N)NC=O
		⚫	\| MeSHName=N'-formylkynurenine
	}}		}}
	\|Section2= {{Chembox Properties		\|Section2={{Chembox Properties
			\| C=11 \| H=12\| N=2\| O=4
	\| Formula=C<sub>11</sub>H<sub>12</sub>N<sub>2</sub>O<sub>4</sub>
			\| Appearance=
	\| MolarMass=236.224 g/mol
	\| ~~Appearance~~=		\| Density=
	\| ~~Density~~=		\| MeltingPt=
	\| ~~MeltingPt~~=		\| BoilingPtC=
	\| ~~BoilingPt~~=		\| Solubility=
	\| Solubility=
	}}		}}
	\|Section3= {{Chembox Hazards		\|Section3={{Chembox Hazards
	\| MainHazards=		\| MainHazards=
	\| FlashPt=		\| FlashPt=
			\| AutoignitionPt =
	\| Autoignition=
	}}		}}
	}}		}}

			'''''{{prime\|N}}''-Formylkynurenine''' is an intermediate in the ] of ]. It is a ] derivative of ]. The formation of ''{{prime\|N}}''-formylkynurenine is catalyzed by ].<ref>{{Cite journal \| doi = 10.1021/ja207066z \| pmid = 21892828 \| title = The Mechanism of Formation of ''N''-Formylkynurenine by Heme Dioxygenases \| journal = Journal of the American Chemical Society \| volume = 133 \| issue = 40 \| pages = 16251–16257 \| year = 2011 \| last1 = Basran \| first1 = Jaswir \| last2 = Efimov \| first2 = Igor \| last3 = Chauhan \| first3 = Nishma \| last4 = Thackray \| first4 = Sarah J \| last5 = Krupa \| first5 = James L \| last6 = Eaton \| first6 = Graham \| last7 = Griffith \| first7 = Gerry A \| last8 = Mowat \| first8 = Christopher G \| last9 = Handa \| first9 = Sandeep \| last10 = Raven \| first10 = Emma Lloyd \| pmc = 3210546\| bibcode = 2011JAChS.13316251B }}</ref>
	'''''N′''-Formylkynurenine''' is an intermediate in the ] of ]. It is a ] derivative of ].

	==See also==		==See also==
	* ]		* ]

	* ]
			==References==
			{{Reflist}}

	{{Amino acid metabolism intermediates}}		{{Amino acid metabolism intermediates}}

	{{DEFAULTSORT:Formylkynurenine, N'-}}		{{DEFAULTSORT:Formylkynurenine, N'-}}
	]		]
			]


	{{biochem-stub}}		{{biochem-stub}}

	]
	]
	]

Latest revision as of 20:42, 24 December 2024

N′-Formylkynurenine
Names

Systematic IUPAC name (2S)-2-Amino-4-(2-formamidophenyl)-4-oxobutanoic acid
Other names N′-Formyl-L-kynurenine
Identifiers
CAS Number	3978-11-8
3D model (JSmol)	Interactive image
ChEBI	CHEBI:30249
ChEMBL	ChEMBL3577708
ChemSpider	388843
KEGG	C02700
MeSH	N'-formylkynurenine
PubChem CID	439788
UNII	PS20W0733S
InChI InChI=1S/C11H12N2O4/c12-8(11(16)17)5-10(15)7-3-1-2-4-9(7)13-6-14/h1-4,6,8H,5,12H2,(H,13,14)(H,16,17)/t8-/m0/s1Key: BYHJHXPTQMMKCA-QMMMGPOBSA-N
SMILES C1=CC=C(C(=C1)C(=O)C(C(=O)O)N)NC=O
Properties
Chemical formula	C₁₁H₁₂N₂O₄
Molar mass	236.227 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Y verify (what is ?) Infobox references

Chemical compound

N′-Formylkynurenine is an intermediate in the catabolism of tryptophan. It is a formylated derivative of kynurenine. The formation of N′-formylkynurenine is catalyzed by heme dioxygenases.

References

Basran, Jaswir; Efimov, Igor; Chauhan, Nishma; Thackray, Sarah J; Krupa, James L; Eaton, Graham; Griffith, Gerry A; Mowat, Christopher G; Handa, Sandeep; Raven, Emma Lloyd (2011). "The Mechanism of Formation of N-Formylkynurenine by Heme Dioxygenases". Journal of the American Chemical Society. 133 (40): 16251–16257. Bibcode:2011JAChS.13316251B. doi:10.1021/ja207066z. PMC 3210546. PMID 21892828.

Amino acid metabolism metabolic intermediates

K→acetyl-CoA

lysine→	Saccharopine Allysine α-Aminoadipic acid 2-Oxoadipic acid Glutaryl-CoA Glutaconyl-CoA Crotonyl-CoA β-Hydroxybutyryl-CoA
leucine→	β-Hydroxy β-methylbutyric acid β-Hydroxy β-methylbutyryl-CoA Isovaleryl-CoA α-Ketoisocaproic acid β-Ketoisocaproic acid β-Ketoisocaproyl-CoA β-Leucine β-Methylcrotonyl-CoA β-Methylglutaconyl-CoA β-Hydroxy β-methylglutaryl-CoA
tryptophan→alanine→	N′-Formylkynurenine Kynurenine Anthranilic acid 3-Hydroxykynurenine 3-Hydroxyanthranilic acid 2-Amino-3-carboxymuconic semialdehyde 2-Aminomuconic semialdehyde 2-Aminomuconic acid Glutaryl-CoA

G→pyruvate→
citrate

glycine→
serine→

3-Phosphoglyceric acid

G→glutamate→
α-ketoglutarate

histidine→	Urocanic acid Imidazol-4-one-5-propionic acid Formiminoglutamic acid Glutamate-1-semialdehyde
proline→	1-Pyrroline-5-carboxylic acid
arginine→	Agmatine Ornithine Citrulline Cadaverine Putrescine
other	cysteine+glutamate→glutathione: γ-Glutamylcysteine

G→propionyl-CoA→
succinyl-CoA

valine→	α-Ketoisovaleric acid Isobutyryl-CoA Methacrylyl-CoA 3-Hydroxyisobutyryl-CoA 3-Hydroxyisobutyric acid 2-Methyl-3-oxopropanoic acid
isoleucine→	2,3-Dihydroxy-3-methylpentanoic acid 2-Methylbutyryl-CoA Tiglyl-CoA 2-Methylacetoacetyl-CoA
methionine→	generation of homocysteine: S-Adenosyl methionine S-Adenosyl-L-homocysteine Homocysteine conversion to cysteine: Cystathionine α-Ketobutyric acid + Cysteine
threonine→	α-Ketobutyric acid
propionyl-CoA→	Methylmalonyl-CoA

G→fumarate

phenylalanine→tyrosine→	4-Hydroxyphenylpyruvic acid Homogentisic acid 4-Maleylacetoacetic acid

G→oxaloacetate

see urea cycle

Other

Cysteine metabolism	Cysteine sulfinic acid

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Latest revision as of 20:42, 24 December 2024

See also

References