Pantetheine

Pantetheine
Names
	Systematic IUPAC name (2R)-2,4-Dihydroxy-3,3-dimethyl-N-{3-oxo-3-[(2-sulfanylethyl)amino]propyl}butanamide
	Other names Pantetheine
Identifiers
CAS Number	496-65-1 R ;
3D model (JSmol)	Interactive image;
3DMet	B00185;
Beilstein Reference	1714196 R
ChEBI	CHEBI:16753 ;
ChemSpider	466 ; 388453 R ;
ECHA InfoCard	100.007.114
EC Number	207-824-1;
KEGG	C00831 ;
MeSH	Pantetheine
PubChem CID	479; 439322 R;
UNII	VCH6X4IARE R ;
	InChI InChI=1S/C11H22N2O4S/c1-11(2,7-14)9(16)10(17)13-4-3-8(15)12-5-6-18/h9,14,16,18H,3-7H2,1-2H3,(H,12,15)(H,13,17) Key: ZNXZGRMVNNHPCA-UHFFFAOYSA-N ;
	SMILES CC(C)(CO)C(O)C(=O)NCCC(=O)NCCS;
Properties
Chemical formula	C11H22N2O4S
Molar mass	278.37 g·mol−1
Related compounds
Related compounds	Pantethine
	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

Pantetheine is the cysteamine amide analog of pantothenic acid (vitamin B₅). The dimer of this compound, pantethine is more commonly known, and is considered to be the most potent form of vitamin B₅. Pantetheine is an intermediate in the catabolism of coenzyme A by the body.^[1]^[2]^[3]

Metabolism

Pantetheine is the product of dephosphorylation of phosphopantetheine:

phosphopantetheine → pantetheine + P_i

In E. coli, this reaction is catalyzed by for example alkaline phosphatase.^[4] The reverse reaction, phosphopantetheine synthesis, is catalyzed by various kinases:^[5]

phosphopantetheine + ATP → pantetheine + ADP

These kinases are able to act upon pantothenoic acid as well and are present in both microorganisms and animal livers.^[5]

Pantetheine is degraded by pantetheinase, which splits it into cysteamine and pantothenic acid:^[3]

pantetheine → cysteamine + pantothenate

Prebiotic evolution

Since pantetheine is a part of coenzyme A, a common cofactor, it is thought to have been present in prebiotic soup. A synthesis mechanism has also been suggested.^[6]

References

^ Hoagland MB, Novelli GD (April 1954). "Biosynthesis of coenzyme A from phospho-pantetheine and of pantetheine from pantothenate". The Journal of Biological Chemistry. 207 (2): 767–773. doi:10.1016/S0021-9258(18)65696-0. PMID 13163064.
^ Cronan JE (June 2014). "The chain-flipping mechanism of ACP (acyl carrier protein)-dependent enzymes appears universal". The Biochemical Journal. 460 (2): 157–163. doi:10.1042/BJ20140239. PMID 24825445.
^ ^a ^b Nitto T, Onodera K (September 2013). "Linkage between coenzyme a metabolism and inflammation: roles of pantetheinase". Journal of Pharmacological Sciences. 123 (1): 1–8. doi:10.1254/jphs.13R01CP. PMID 23978960.
^ Jackowski S, Rock CO (April 1984). "Metabolism of 4'-phosphopantetheine in Escherichia coli". Journal of Bacteriology. 158 (1): 115–120. doi:10.1128/jb.158.1.115-120.1984. PMC 215387. PMID 6370952.
^ ^a ^b Brown GM (1970-01-01), Florkin M, Stotz EH (eds.), "Section d - Biosynthesis of Pantothenic Acid and Coenzyme A", Comprehensive Biochemistry, Metabolism of Vitamins and Trace Elements, vol. 21, Elsevier, pp. 73–80, doi:10.1016/b978-0-444-40871-6.50012-x, retrieved 2023-10-29
^ Keefe AD, Newton GL, Miller SL (February 1995). "A possible prebiotic synthesis of pantetheine, a precursor to coenzyme A". Nature. 373 (6516): 683–685. Bibcode:1995Natur.373..683K. doi:10.1038/373683a0. PMID 7854449. S2CID 4255864.

[1] Hoagland MB, Novelli GD (April 1954). "Biosynthesis of coenzyme A from phospho-pantetheine and of pantetheine from pantothenate". The Journal of Biological Chemistry. 207 (2): 767–773. doi:10.1016/S0021-9258(18)65696-0. PMID 13163064.

[2] Cronan JE (June 2014). "The chain-flipping mechanism of ACP (acyl carrier protein)-dependent enzymes appears universal". The Biochemical Journal. 460 (2): 157–163. doi:10.1042/BJ20140239. PMID 24825445.

[Nitto_2013-3] Nitto T, Onodera K (September 2013). "Linkage between coenzyme a metabolism and inflammation: roles of pantetheinase". Journal of Pharmacological Sciences. 123 (1): 1–8. doi:10.1254/jphs.13R01CP. PMID 23978960.

[4] Jackowski S, Rock CO (April 1984). "Metabolism of 4'-phosphopantetheine in Escherichia coli". Journal of Bacteriology. 158 (1): 115–120. doi:10.1128/jb.158.1.115-120.1984. PMC 215387. PMID 6370952.

[Brown_1970-5] Brown GM (1970-01-01), Florkin M, Stotz EH (eds.), "Section d - Biosynthesis of Pantothenic Acid and Coenzyme A", Comprehensive Biochemistry, Metabolism of Vitamins and Trace Elements, vol. 21, Elsevier, pp. 73–80, doi:10.1016/b978-0-444-40871-6.50012-x, retrieved 2023-10-29

[6] Keefe AD, Newton GL, Miller SL (February 1995). "A possible prebiotic synthesis of pantetheine, a precursor to coenzyme A". Nature. 373 (6516): 683–685. Bibcode:1995Natur.373..683K. doi:10.1038/373683a0. PMID 7854449. S2CID 4255864.

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