Chemistry:Methylcrotonyl-CoA

Methylcrotonyl-CoA
Names
	IUPAC name 3′-O-Phosphonoadenosine 5′-[(3R)-3-hydroxy-2-methyl-4-{[3-({2-[(3-methylbut-2-enoyl)sulfanyl]ethyl}amino)-3-oxopropyl]amino}-4-oxobutyl dihydrogen diphosphate]
	Preferred IUPAC name O1-{[(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methyl} O3-[(3R)-3-hydroxy-2-methyl-4-{[3-({2-[(3-methylbut-2-enoyl)sulfanyl]ethyl}amino)-3-oxopropyl]amino}-4-oxobutyl] dihydrogen diphosphate
Identifiers
CAS Number	6712-03-4;
3D model (JSmol)	Interactive image;
MeSH	Methylcrotonyl-CoA
PubChem CID	439869;
	InChI InChI=1S/C26H42N7O17P3S/c1-14(2)9-17(35)54-8-7-28-16(34)5-6-29-24(38)21(37)26(3,4)11-47-53(44,45)50-52(42,43)46-10-15-20(49-51(39,40)41)19(36)25(48-15)33-13-32-18-22(27)30-12-31-23(18)33/h9,12-13,15,19-21,25,36-37H,5-8,10-11H2,1-4H3,(H,28,34)(H,29,38)(H,42,43)(H,44,45)(H2,27,30,31)(H2,39,40,41)/t15-,19-,20-,21?,25-/m1/s1 Key: BXIPALATIYNHJN-TVCSPYKZSA-N;
	SMILES CC(=CC(=O)SCCNC(=O)CCNC(=O)C(C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=CN=C32)N)O)OP(=O)(O)O)O)C;
Properties
Chemical formula	C26H42N7O17P3S
Molar mass	849.636 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

3-Methylcrotonyl-CoA (β-Methylcrotonyl-CoA or MC-CoA) is an intermediate in the metabolism of leucine.^[1]^[2]^[3]

It is found in mitochondria, where it is formed from isovaleryl-coenzyme A by isovaleryl coenzyme A dehydrogenase. It then reacts with CO₂ to yield 3-Methylcrotonyl-CoA carboxylase. ^[4]

Leucine metabolism

Leucine metabolism in humans

L-Leucine

Branched-chain amino
acid aminotransferase

Muscle: α-Ketoisocaproate (α-KIC)

Liver: α-Ketoisocaproate (α-KIC)

Branched-chain α-ketoacid
dehydrogenase (mitochondria)

KIC-dioxygenase
(cytosol)

Isovaleryl-CoA

β-Hydroxy
β-methylbutyrate
(HMB)

Excreted
in urine
(10–40%)

HMB-CoA

β-Hydroxy β-methylglutaryl-CoA
(HMG-CoA)

β-Methylcrotonyl-CoA
(MC-CoA)

β-Methylglutaconyl-CoA
(MG-CoA)

CO₂

O₂

CO₂

H₂O

CO₂

H₂O

(liver)
HMG-CoA
lyase

Enoyl-CoA hydratase

Isovaleryl-CoA
dehydrogenase

β-Hydroxybutyrate
dehydrogenase

Unknown
enzyme

Human metabolic pathway for HMB and isovaleryl-CoA relative to L-leucine.^[1]^[2]^[3] Of the two major pathways, L-leucine is mostly metabolized into isovaleryl-CoA, while only about 5% is metabolized into HMB.^[1]^[2]^[3]

References

↑ ^1.0 ^1.1 ^1.2 "International Society of Sports Nutrition Position Stand: beta-hydroxy-beta-methylbutyrate (HMB)". Journal of the International Society of Sports Nutrition 10 (1): 6. February 2013. doi:10.1186/1550-2783-10-6. PMID 23374455.
↑ ^2.0 ^2.1 ^2.2 "HMB supplementation: clinical and athletic performance-related effects and mechanisms of action". Amino Acids 40 (4): 1015–1025. April 2011. doi:10.1007/s00726-010-0678-0. PMID 20607321. https://repositorio.unal.edu.co/handle/unal/77957. "HMB is a metabolite of the amino acid leucine (Van Koverin and Nissen 1992), an essential amino acid. The first step in HMB metabolism is the reversible transamination of leucine to [α-KIC] that occurs mainly extrahepatically (Block and Buse 1990). Following this enzymatic reaction, [α-KIC] may follow one of two pathways. In the first, HMB is produced from [α-KIC] by the cytosolic enzyme KIC dioxygenase (Sabourin and Bieber 1983). The cytosolic dioxygenase has been characterized extensively and differs from the mitochondrial form in that the dioxygenase enzyme is a cytosolic enzyme, whereas the dehydrogenase enzyme is found exclusively in the mitochondrion (Sabourin and Bieber 1981, 1983). Importantly, this route of HMB formation is direct and completely dependent of liver KIC dioxygenase. Following this pathway, HMB in the cytosol is first converted to cytosolic β-hydroxy-β-methylglutaryl-CoA (HMG-CoA), which can then be directed for cholesterol synthesis (Rudney 1957) (Fig. 1). In fact, numerous biochemical studies have shown that HMB is a precursor of cholesterol (Zabin and Bloch 1951; Nissen et al. 2000).". Cite error: Invalid <ref> tag; name "HMB athletic performance-related effects 2011 review" defined multiple times with different content
↑ ^3.0 ^3.1 ^3.2 Nutrient Metabolism: Structures, Functions, and Genes (2nd ed.). Academic Press. May 2015. pp. 385–388. ISBN 978-0-12-387784-0. https://books.google.com/books?id=aTQTAAAAQBAJ&printsec=frontcover#v=onepage. Retrieved 6 June 2016. "Energy fuel: Eventually, most Leu is broken down, providing about 6.0kcal/g. About 60% of ingested Leu is oxidized within a few hours ... Ketogenesis: A significant proportion (40% of an ingested dose) is converted into acetyl-CoA and thereby contributes to the synthesis of ketones, steroids, fatty acids, and other compounds"
Figure 8.57: Metabolism of L-leucine
↑ "3-methylcrotonyl-CoA carboxylase deficiency: clinical, biochemical, enzymatic and molecular studies in 88 individuals". Orphanet Journal of Rare Diseases 7 (1): 31. May 2012. doi:10.1186/1750-1172-7-31. PMID 22642865.

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Original source: https://en.wikipedia.org/wiki/Methylcrotonyl-CoA. Read more

[ISSN_position_stand_2013-1] 1.0 ^1.1 ^1.2 "International Society of Sports Nutrition Position Stand: beta-hydroxy-beta-methylbutyrate (HMB)". Journal of the International Society of Sports Nutrition 10 (1): 6. February 2013. doi:10.1186/1550-2783-10-6. PMID 23374455.

[HMB_athletic_performance-related_effects_2011_review-2] 2.0 ^2.1 ^2.2 "HMB supplementation: clinical and athletic performance-related effects and mechanisms of action". Amino Acids 40 (4): 1015–1025. April 2011. doi:10.1007/s00726-010-0678-0. PMID 20607321. https://repositorio.unal.edu.co/handle/unal/77957. "HMB is a metabolite of the amino acid leucine (Van Koverin and Nissen 1992), an essential amino acid. The first step in HMB metabolism is the reversible transamination of leucine to [α-KIC] that occurs mainly extrahepatically (Block and Buse 1990). Following this enzymatic reaction, [α-KIC] may follow one of two pathways. In the first, HMB is produced from [α-KIC] by the cytosolic enzyme KIC dioxygenase (Sabourin and Bieber 1983). The cytosolic dioxygenase has been characterized extensively and differs from the mitochondrial form in that the dioxygenase enzyme is a cytosolic enzyme, whereas the dehydrogenase enzyme is found exclusively in the mitochondrion (Sabourin and Bieber 1981, 1983). Importantly, this route of HMB formation is direct and completely dependent of liver KIC dioxygenase. Following this pathway, HMB in the cytosol is first converted to cytosolic β-hydroxy-β-methylglutaryl-CoA (HMG-CoA), which can then be directed for cholesterol synthesis (Rudney 1957) (Fig. 1). In fact, numerous biochemical studies have shown that HMB is a precursor of cholesterol (Zabin and Bloch 1951; Nissen et al. 2000).". Cite error: Invalid <ref> tag; name "HMB athletic performance-related effects 2011 review" defined multiple times with different content

[Leucine_metabolism-3] 3.0 ^3.1 ^3.2 Nutrient Metabolism: Structures, Functions, and Genes (2nd ed.). Academic Press. May 2015. pp. 385–388. ISBN 978-0-12-387784-0. https://books.google.com/books?id=aTQTAAAAQBAJ&printsec=frontcover#v=onepage. Retrieved 6 June 2016. "Energy fuel: Eventually, most Leu is broken down, providing about 6.0kcal/g. About 60% of ingested Leu is oxidized within a few hours ... Ketogenesis: A significant proportion (40% of an ingested dose) is converted into acetyl-CoA and thereby contributes to the synthesis of ketones, steroids, fatty acids, and other compounds"
Figure 8.57: Metabolism of L-leucine

[4] "3-methylcrotonyl-CoA carboxylase deficiency: clinical, biochemical, enzymatic and molecular studies in 88 individuals". Orphanet Journal of Rare Diseases 7 (1): 31. May 2012. doi:10.1186/1750-1172-7-31. PMID 22642865.

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Chemistry:Methylcrotonyl-CoA

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Names

IUPAC name 3′-O-Phosphonoadenosine 5′-[(3R)-3-hydroxy-2-methyl-4-{[3-({2-[(3-methylbut-2-enoyl)sulfanyl]ethyl}amino)-3-oxopropyl]amino}-4-oxobutyl dihydrogen diphosphate]
Preferred IUPAC name O¹-{[(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methyl} O³-[(3R)-3-hydroxy-2-methyl-4-{[3-({2-[(3-methylbut-2-enoyl)sulfanyl]ethyl}amino)-3-oxopropyl]amino}-4-oxobutyl] dihydrogen diphosphate
Identifiers
CAS Number	6712-03-4
3D model (JSmol)	Interactive image
MeSH	Methylcrotonyl-CoA
PubChem CID	439869
InChI InChI=1S/C26H42N7O17P3S/c1-14(2)9-17(35)54-8-7-28-16(34)5-6-29-24(38)21(37)26(3,4)11-47-53(44,45)50-52(42,43)46-10-15-20(49-51(39,40)41)19(36)25(48-15)33-13-32-18-22(27)30-12-31-23(18)33/h9,12-13,15,19-21,25,36-37H,5-8,10-11H2,1-4H3,(H,28,34)(H,29,38)(H,42,43)(H,44,45)(H2,27,30,31)(H2,39,40,41)/t15-,19-,20-,21?,25-/m1/s1 Key: BXIPALATIYNHJN-TVCSPYKZSA-N
SMILES CC(=CC(=O)SCCNC(=O)CCNC(=O)C(C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=CN=C32)N)O)OP(=O)(O)O)O)C
Properties
Chemical formula	C₂₆H₄₂N₇O₁₇P₃S
Molar mass	849.636 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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