Cystathionine: Difference between revisions

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	{{chembox		{{chembox
			\| Verifiedfields = changed
⚫	\| verifiedrevid = ~~414094014~~
			\| Watchedfields = changed
		⚫	\| verifiedrevid = 443553935
	\| ImageFile_Ref = {{chemboximage\|correct\|??}}		\| ImageFile_Ref = {{chemboximage\|correct\|??}}
	\| ImageFile=~~Cystathionine~~.~~png~~		\| ImageFile = Cystathionin.svg
			\| ImageSize = 220
	\|ImageName=Skeletal formula
			\| ImageAlt = Skeletal formula of cystathionine
	\|ImageFile1=Cystathionine-3D~~-balls~~.png		\| ImageFile1 = Cystathionine zwitterion 3D ball.png
	\|ImageSize1=~~230px~~		\| ImageSize1 = 240px
	\|ImageName1=Ball-and-stick model
			\| ImageAlt1=Ball-and-stick model of the cystathionine molecule as a zwitterion
	\|IUPACName=2-amino-4-(2-amino-2-carboxy-ethyl) thio-butanoic acid
	\|OtherNames=<small>L</small>-Cystathionine; ''S''--<small>L</small>-homocysteine		\| IUPACName=S-((R)-2-amino-2-carboxyethyl)-L-homocysteine
			\| OtherNames=<small>L</small>-Cystathionine; ''S''--<small>L</small>-homocysteine
	\|Section1= {{Chembox Identifiers		\|Section1={{Chembox Identifiers
	\| KEGG_Ref = {{keggcite\|correct\|kegg}}		\| KEGG_Ref = {{keggcite\|correct\|kegg}}
	\| KEGG = C00542		\| KEGG = C00542
	\| InChI = 1/C7H14N2O4S/c8-4(6(10)11)1-2-14-3-5(9)7(12)13/h4-5H,1-3,8-9H2,(H,10,11)(H,12,13)		\| InChI = 1/C7H14N2O4S/c8-4(6(10)11)1-2-14-3-5(9)7(12)13/h4-5H,1-3,8-9H2,(H,10,11)(H,12,13)
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	\| ChEMBL_Ref = {{ebicite\|correct\|EBI}}		\| ChEMBL_Ref = {{ebicite\|correct\|EBI}}
	\| ChEMBL = 209241		\| ChEMBL = 209241
	\| StdInChI_Ref = {{stdinchicite\|~~correct~~\|chemspider}}		\| StdInChI_Ref = {{stdinchicite\|changed\|chemspider}}
	\| StdInChI = 1S/C7H14N2O4S/c8-4(6(10)11)1-2-14-3-5(9)7(12)13/h4-5H,1-3,8-9H2,(H,10,11)(H,12,13)		\| StdInChI = 1S/C7H14N2O4S/c8-4(6(10)11)1-2-14-3-5(9)7(12)13/h4-5H,1-3,8-9H2,(H,10,11)(H,12,13)/t4-,5-/m0/s1
	\| StdInChIKey_Ref = {{stdinchicite\|~~correct~~\|chemspider}}		\| StdInChIKey_Ref = {{stdinchicite\|changed\|chemspider}}
	\| StdInChIKey = ILRYLPWNYFXEMH-~~UHFFFAOYSA~~-N		\| StdInChIKey = ILRYLPWNYFXEMH-WHFBIAKZSA-N
	\| CASNo_Ref = {{cascite\|correct\|CAS}}		\| CASNo_Ref = {{cascite\|correct\|CAS}}
	\| CASNo=56-88-2		\| CASNo=56-88-2
			\| UNII_Ref = {{fdacite\|correct\|FDA}}
⚫	\| PubChem=~~834~~
			\| UNII = 375YFJ481O
⚫	\| ChemSpiderID_Ref = {{chemspidercite\|~~correct~~\|chemspider}}
		⚫	\| PubChem=439258
⚫	\| ChemSpiderID = ~~811~~
		⚫	\| ChemSpiderID_Ref = {{chemspidercite\|changed\|chemspider}}
⚫	\| ChEBI = 17755
		⚫	\| ChemSpiderID = 388392
⚫	\| SMILES = O=C(O)C(N)~~CSCCC~~(C(=O)O)N
			\| ChEBI_Ref = {{ebicite\|correct\|EBI}}
⚫	\| MeSHName=Cystathionine
		⚫	\| ChEBI = 17755
		⚫	\| SMILES = C(CSC(C(=O)O)N)(C(=O)O)N
		⚫	\| MeSHName=Cystathionine
	}}		}}
	\|Section2= {{Chembox Properties		\|Section2={{Chembox Properties
			\| C=7\|H=14\|N=2\|O=4\|S=1
	\| Formula=C<sub>7</sub>H<sub>14</sub>N<sub>2</sub>O<sub>4</sub>S
			\| Appearance=
	\| MolarMass=222.263 g/mol
	\| ~~Appearance~~=		\| Density=
	\| ~~Density~~=		\| MeltingPt=
	\| ~~MeltingPt~~=		\| BoilingPt=
	\| ~~BoilingPt~~=		\| Solubility=
	\| Solubility=
	}}		}}
	\|Section3= {{Chembox Hazards		\|Section3={{Chembox Hazards
	\| MainHazards=		\| MainHazards=
	\| FlashPt=		\| FlashPt=
			\| AutoignitionPt =
	\| Autoignition=
	}}		}}
	}}		}}
	'''Cystathionine''' is an intermediate in the synthesis of ].

	It is ~~generated~~ from ] and ~~serine~~ by ].		'''Cystathionine''' is an intermediate in the synthesis of ] from ]. It is produced by the ] and is converted into cysteine by ] (CTH).

	It is cleaved into ] and ] by ].		Biosynthetically, cystathionine is generated from ] and ] by ] (upper reaction in the diagram below). It is then cleaved into ] and ] by ] (lower reaction).

	An excess in the urine is called ].		An excess of cystathionine in the urine is called ].

	] catalyzes the upper reaction and ] catalyzes the lower reaction.]]		] catalyzes the upper reaction and ] catalyzes the lower reaction.]]{{clear-left}}

			] (CDO), and ] can turn cysteine into ] and then ].<ref>{{ Cite journal \| author = Harris Ripps, Wen Shen \|date = 2012 \| title = Review: Taurine: A "very essential" amino acid \| journal = Molecular Vision \|volume = 18 \| pages = 2673–2686 \| pmid=23170060 \| pmc=3501277}}</ref> Alternately, the cysteine from the cystathionine gamma-lyase can be used by the enzymes ] (GCL) and ] (GSS) to produce ].
⚫	{{Amino acid metabolism intermediates}}

			==References==
			{{Reflist}}

		⚫	{{Amino acid metabolism intermediates}}

			]
	{{biochem-stub}}

	]		]
			]

			]
	]
			]
	]

Latest revision as of 14:32, 25 November 2024

Cystathionine
Names


IUPAC name S-((R)-2-amino-2-carboxyethyl)-L-homocysteine
Other names L-Cystathionine; S--L-homocysteine
Identifiers
CAS Number	56-88-2
3D model (JSmol)	Interactive image
ChEBI	CHEBI:17755
ChEMBL	ChEMBL209241
ChemSpider	388392
ECHA InfoCard	100.000.269
KEGG	C00542
MeSH	Cystathionine
PubChem CID	439258
UNII	375YFJ481O
CompTox Dashboard (EPA)	DTXSID20971384
InChI InChI=1S/C7H14N2O4S/c8-4(6(10)11)1-2-14-3-5(9)7(12)13/h4-5H,1-3,8-9H2,(H,10,11)(H,12,13)/t4-,5-/m0/s1Key: ILRYLPWNYFXEMH-WHFBIAKZSA-N InChI=1/C7H14N2O4S/c8-4(6(10)11)1-2-14-3-5(9)7(12)13/h4-5H,1-3,8-9H2,(H,10,11)(H,12,13)Key: ILRYLPWNYFXEMH-UHFFFAOYAH
SMILES C(CSC(C(=O)O)N)(C(=O)O)N
Properties
Chemical formula	C₇H₁₄N₂O₄S
Molar mass	222.26 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is ?) Infobox references

Chemical compound

Cystathionine is an intermediate in the synthesis of cysteine from homocysteine. It is produced by the transsulfuration pathway and is converted into cysteine by cystathionine gamma-lyase (CTH).

Biosynthetically, cystathionine is generated from homocysteine and serine by cystathionine beta synthase (upper reaction in the diagram below). It is then cleaved into cysteine and α-ketobutyrate by cystathionine gamma-lyase (lower reaction).

An excess of cystathionine in the urine is called cystathioninuria.

Cysteine dioxygenase (CDO), and sulfinoalanine decarboxylase can turn cysteine into hypotaurine and then taurine. Alternately, the cysteine from the cystathionine gamma-lyase can be used by the enzymes glutamate–cysteine ligase (GCL) and glutathione synthetase (GSS) to produce glutathione.

References

Harris Ripps, Wen Shen (2012). "Review: Taurine: A "very essential" amino acid". Molecular Vision. 18: 2673–2686. PMC 3501277. PMID 23170060.

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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