Β-Hydroxybutyryl-CoA: Difference between revisions

Browse history interactively ← Previous editContent deleted Content addedVisual WikitextInline

Revision as of 00:28, 23 April 2012 editThehelpfulbot (talk \| contribs)56,901 editsm r2.6.5) (Robot: Adding fa:بتا-هیدروکسی‌بوتیریل-کوآ ← Previous edit		Latest revision as of 09:49, 4 September 2023 edit undoSilverLocust (talk \| contribs)Administrators25,136 edits displaytitle
(18 intermediate revisions by 14 users not shown)
Line 1:		Line 1:
			{{lowercase title}}
⚫	~~{{DISPLAYTITLE:''beta''~~-Hydroxybutyryl-CoA}}
	{{chembox		{{chembox
			\| Verifiedfields = changed
⚫	\| verifiedrevid = ~~329754364~~
			\| Watchedfields = changed
	\|Name=β-Hydroxybutyryl-CoA
		⚫	\| verifiedrevid = 432802244
⚫	\|ImageFile=3-hydroxybutyryl coenzyme A.svg
		⚫	\| Name = β-Hydroxybutyryl-CoA
⚫	\|ImageSize=300px
		⚫	\| ImageFile = 3-hydroxybutyryl coenzyme A.svg
	\|IUPACName=
		⚫	\| ImageSize = 300px
⚫	\|OtherNames=
			\| IUPACName = <nowiki>{sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid</nowiki>
⚫	\|Section1= {{Chembox ~~Identifiers2~~
		⚫	\| OtherNames =
⚫	\| CASNo=2871-66-1
			\| SystematicName =
⚫	\| PubChem=644065
		⚫	\| Section1 = {{Chembox Identifiers
⚫	\|InChI=1/C25H42N7O18P3S/c1-13(33)8-16(35)54-7-6-27-15(34)4-5-28-23(38)20(37)25(2,3)10-47-53(44,45)50-52(42,43)46-9-14-19(49-51(39,40)41)18(36)24(48-14)32-12-31-17-21(26)29-11-30-22(17)32/h11-14,18-20,24,33,36-37H,4-10H2,1-3H3,(H,27,34)(H,28,38)(H,42,43)(H,44,45)(H2,26,29,30)(H2,39,40,41)/t13-,14-,18-,19-,20?,24-/m1/s1
			\| CASNo_Ref = {{cascite\|changed\|??}}
⚫	\| InChIKey = QHHKKMYHDBRONY-JYMPOPDUBN
		⚫	\| CASNo=2871-66-1
		⚫	\| PubChem=644065
		⚫	\| InChI=1/C25H42N7O18P3S/c1-13(33)8-16(35)54-7-6-27-15(34)4-5-28-23(38)20(37)25(2,3)10-47-53(44,45)50-52(42,43)46-9-14-19(49-51(39,40)41)18(36)24(48-14)32-12-31-17-21(26)29-11-30-22(17)32/h11-14,18-20,24,33,36-37H,4-10H2,1-3H3,(H,27,34)(H,28,38)(H,42,43)(H,44,45)(H2,26,29,30)(H2,39,40,41)/t13-,14-,18-,19-,20?,24-/m1/s1
		⚫	\| InChIKey = QHHKKMYHDBRONY-JYMPOPDUBN
	}}		}}
	\|Section2= {{Chembox Properties		\| Section2 = {{Chembox Properties
	\| Formula=C<sub>25</sub>H<sub>42</sub>N<sub>7</sub>O<sub>18</sub>P<sub>3</sub>S		\| Formula=C<sub>25</sub>H<sub>42</sub>N<sub>7</sub>O<sub>18</sub>P<sub>3</sub>S
	\| MolarMass=853.625 g/mol		\| MolarMass=853.625 g/mol
	\| Appearance=		\| Appearance=
	\| Density=		\| Density=
	\| MeltingPt=		\| MeltingPt=
	\| BoilingPt=		\| BoilingPt=
	\| Solubility=		\| Solubility=
	}}		}}
	\|Section3= {{Chembox Hazards		\| Section3 = {{Chembox Hazards
	\| MainHazards=		\| MainHazards=
	\| FlashPt=		\| FlashPt=
			\| AutoignitionPt =
	\| Autoignition=
	}}		}}
			\| Section4 =
			\| Section5 =
			\| Section6 =
	}}		}}

			'''β-Hydroxybutyryl-CoA''' (or '''3-hydroxybutyryl-coenzyme A''') is an intermediate in the ] of ], and in the metabolism of ] and ].<ref>{{Cite journal \|last1=Numa \|first1=S. \|last2=Ishimura \|first2=Y. \|last3=Nishizuka \|first3=Y. \|last4=Hayaishi \|first4=O. \|date=1961-10-23 \|title=beta-Hydroxybutyryl-CoA, an intermediate in glutarate catabolism \|url=https://pubmed.ncbi.nlm.nih.gov/14480702/ \|journal=Biochemical and Biophysical Research Communications \|volume=6 \|pages=38–43 \|doi=10.1016/0006-291x(61)90181-4 \|issn=0006-291X \|pmid=14480702}}</ref><ref>{{Cite journal \|last1=Liu \|first1=Shumeng \|last2=Yu \|first2=Huajing \|last3=Liu \|first3=Yongqing \|last4=Liu \|first4=Xinhua \|last5=Zhang \|first5=Yu \|last6=Bu \|first6=Chen \|last7=Yuan \|first7=Shuai \|last8=Chen \|first8=Zhe \|last9=Xie \|first9=Guojia \|last10=Li \|first10=Wanjin \|last11=Xu \|first11=Bosen \|last12=Yang \|first12=Jianguo \|last13=He \|first13=Lin \|last14=Jin \|first14=Tong \|last15=Xiong \|first15=Yundong \|date=2017-09-07 \|title=Chromodomain Protein CDYL Acts as a Crotonyl-CoA Hydratase to Regulate Histone Crotonylation and Spermatogenesis \|journal=Molecular Cell \|volume=67 \|issue=5 \|pages=853–866.e5 \|doi=10.1016/j.molcel.2017.07.011 \|issn=1097-4164 \|pmid=28803779\|doi-access=free }}</ref> The L-3-hydroxybutyl-CoA (or (S)-3-hydroxybutanoyl-CoA) enantiomer is also the second to last intermediate in ] of even-numbered, straight chain, and saturated fatty acids.<ref>{{Cite journal \|last1=van Rijt \|first1=Willemijn J. \|last2=Van Hove \|first2=Johan L. K. \|last3=Vaz \|first3=Frédéric M. \|last4=Havinga \|first4=Rick \|last5=Allersma \|first5=Derk P. \|last6=Zijp \|first6=Tanja R. \|last7=Bedoyan \|first7=Jirair K. \|last8=Heiner-Fokkema \|first8=M. R. \|last9=Reijngoud \|first9=Dirk-Jan \|last10=Geraghty \|first10=Michael T. \|last11=Wanders \|first11=Ronald J. A. \|last12=Oosterveer \|first12=Maaike H. \|last13=Derks \|first13=Terry G. J. \|date=July 2021 \|title=Enantiomer-specific pharmacokinetics of D,L-3-hydroxybutyrate: Implications for the treatment of multiple acyl-CoA dehydrogenase deficiency \|journal=Journal of Inherited Metabolic Disease \|volume=44 \|issue=4 \|pages=926–938 \|doi=10.1002/jimd.12365 \|issn=1573-2665 \|pmc=8359440 \|pmid=33543789}}</ref>
	'''β-Hydroxybutyryl-CoA''' (or '''3-hydroxybutyryl-coenzyme A''') is an intermediate in the ] of ], and in the metabolism of ] and ].

	==See also==		==See also==
Line 36:		Line 43:
	* ]		* ]

			==References==
	<!-- Metadata: see ] --->
			{{Reflist}}
	{{InChI\|
	InChI=1/C25H42N7O18P3S/c1-13(33)8-16(35)54-7-6-27-15(34)4-5-28-23(38)20(37)25(2,3)10-47-53(44,45)50-52(42,43)46-9-14-19(49-51(39,40)41)18(36)24(48-14)32-12-31-17-21(26)29-11-30-22(17)32/h11-14,18-20,24,33,36-37H,4-10H2,1-3H3,(H,27,34)(H,28,38)(H,42,43)(H,44,45)(H2,26,29,30)(H2,39,40,41)/t13-,14-,18-,19-,20?,24-/m1/s1
	}}

	{{Amino acid metabolism intermediates}}		{{Amino acid metabolism intermediates}}
Line 46:		Line 51:
	]		]
	]		]
	]		]

	]

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

	]
	]
	]

Latest revision as of 09:49, 4 September 2023

β-Hydroxybutyryl-CoA
Names

IUPAC name {sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
Identifiers
CAS Number	2871-66-1
PubChem CID	644065
CompTox Dashboard (EPA)	DTXSID90951355
InChI InChI=1/C25H42N7O18P3S/c1-13(33)8-16(35)54-7-6-27-15(34)4-5-28-23(38)20(37)25(2,3)10-47-53(44,45)50-52(42,43)46-9-14-19(49-51(39,40)41)18(36)24(48-14)32-12-31-17-21(26)29-11-30-22(17)32/h11-14,18-20,24,33,36-37H,4-10H2,1-3H3,(H,27,34)(H,28,38)(H,42,43)(H,44,45)(H2,26,29,30)(H2,39,40,41)/t13-,14-,18-,19-,20?,24-/m1/s1Key: QHHKKMYHDBRONY-JYMPOPDUBN
Properties
Chemical formula	C₂₅H₄₂N₇O₁₈P₃S
Molar mass	853.625 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

β-Hydroxybutyryl-CoA (or 3-hydroxybutyryl-coenzyme A) is an intermediate in the fermentation of butyric acid, and in the metabolism of lysine and tryptophan. The L-3-hydroxybutyl-CoA (or (S)-3-hydroxybutanoyl-CoA) enantiomer is also the second to last intermediate in beta oxidation of even-numbered, straight chain, and saturated fatty acids.

References

Numa, S.; Ishimura, Y.; Nishizuka, Y.; Hayaishi, O. (1961-10-23). "beta-Hydroxybutyryl-CoA, an intermediate in glutarate catabolism". Biochemical and Biophysical Research Communications. 6: 38–43. doi:10.1016/0006-291x(61)90181-4. ISSN 0006-291X. PMID 14480702.
Liu, Shumeng; Yu, Huajing; Liu, Yongqing; Liu, Xinhua; Zhang, Yu; Bu, Chen; Yuan, Shuai; Chen, Zhe; Xie, Guojia; Li, Wanjin; Xu, Bosen; Yang, Jianguo; He, Lin; Jin, Tong; Xiong, Yundong (2017-09-07). "Chromodomain Protein CDYL Acts as a Crotonyl-CoA Hydratase to Regulate Histone Crotonylation and Spermatogenesis". Molecular Cell. 67 (5): 853–866.e5. doi:10.1016/j.molcel.2017.07.011. ISSN 1097-4164. PMID 28803779.
van Rijt, Willemijn J.; Van Hove, Johan L. K.; Vaz, Frédéric M.; Havinga, Rick; Allersma, Derk P.; Zijp, Tanja R.; Bedoyan, Jirair K.; Heiner-Fokkema, M. R.; Reijngoud, Dirk-Jan; Geraghty, Michael T.; Wanders, Ronald J. A.; Oosterveer, Maaike H.; Derks, Terry G. J. (July 2021). "Enantiomer-specific pharmacokinetics of D,L-3-hydroxybutyrate: Implications for the treatment of multiple acyl-CoA dehydrogenase deficiency". Journal of Inherited Metabolic Disease. 44 (4): 926–938. doi:10.1002/jimd.12365. ISSN 1573-2665. PMC 8359440. PMID 33543789.

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

This biochemistry article is a stub. You can help Misplaced Pages by expanding it.

Categories:

Latest revision as of 09:49, 4 September 2023

See also

References