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). verify (what is ?) 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 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

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

(

HMG-CoA
lyase

Enoyl-CoA hydratase

Isovaleryl-CoA
dehydrogenase

β-Hydroxybutyrate
dehydrogenase

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

References

^
PMID 23374455
.

S2CID 11120110
. 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).

^
ISBN 978-0-12-387784-0. 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

PMID 22642865
.

^
S2CID 11120110
. 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).

v
t
e
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

citrate
glycine→
serine→

3-Phosphoglyceric acid

glycine→creatine: Glycocyamine

Phosphocreatine

Creatinine

G→
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

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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v
t
e

Retrieved from "https://en.wikipedia.org/w/index.php?title=Methylcrotonyl-CoA&oldid=1188129905"

[ISSN_position_stand_2013-1] 
PMID 23374455
.

[HMB_athletic_performance-related_effects_2011_review-2] S2CID 11120110
. 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).

[Leucine_metabolism-3] 
ISBN 978-0-12-387784-0. 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] PMID 22642865
.

[HMB_athletic_performance-related_effects_2011_reviewb-5] 
S2CID 11120110
. 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).

[1]

[2]

[3]

[4]

[5]

Leucine metabolism

See also

References