Dopastin

Dopastin
Names
	Preferred IUPAC name (2E)-N-{(2S)-2-[Hydroxy(nitroso)amino]-3-methylbutyl}but-2-enamide
Identifiers
CAS Number	37134-80-8 ;
3D model (JSmol)	Interactive image;
ChemSpider	4939169;
PubChem CID	6434226;
UNII	F8KR5E0EHC ;
CompTox Dashboard (EPA)	DTXSID001029849 ;
	InChI InChI=1S/C9H17N3O3/c1-4-5-9(13)10-6-8(7(2)3)12(15)11-14/h4-5,7-8,15H,6H2,1-3H3,(H,10,13)/b5-4+/t8-/m1/s1 Key: FJUBKTNNXRFHFD-WTSVBCDHSA-N; InChI=1/C9H17N3O3/c1-4-5-9(13)10-6-8(7(2)3)12(15)11-14/h4-5,7-8,15H,6H2,1-3H3,(H,10,13)/b5-4+/t8-/m1/s1 Key: FJUBKTNNXRFHFD-WTSVBCDHBR;
	SMILES O=C(NC[C@@H](N(O)N=O)C(C)C)/C=C/C;
Properties
Chemical formula	C9H17N3O3
Molar mass	215.253 g·mol−1
Melting point	116 to 119 °C (241 to 246 °F; 389 to 392 K)
Acidity (pKa)	5.1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Dopastin is a chemical compound produced by the bacteria Pseudomonas No. BAC-125.^[2] It was first isolated and characterized in 1972. It is an inhibitor of the enzyme dopamine β-hydroxylase.^[3]

Dopastin can be prepared synthetically from L-valinol.^[4]

References

^ ^a ^b Merck Index, 11th Edition, 3417
^ Iimura, H; Takeuchi, T; Kondo, S; Matsuzaki, M; Umezawa, H (1972). "Dopastin, an inhibitor of dopamine -hydroxylase". The Journal of Antibiotics. 25 (8): 497–500. doi:10.7164/antibiotics.25.497. PMID 4648494.
^ H. Iinuma; M. Matsuzaki; T. Nagatsu; T. Takeuchi; H. Umezawa (1974). "Biochemical and biological studies on dopastin, an inhibitor of dopamine β-hydroxylase". Agric. Biol. Chem. 38 (11): 2107–2111. doi:10.1271/bbb1961.38.2107.
^ Ohno, M.; Iinuma, H.; Yagisawa, N.; Shibahara, S.; Suhara, Y.; Kondo, S.; Maeda, K.; Umezawa, H. (1973). "Synthesis of dopastin, a dopamine ?-hydroxylase inhibitor of microbial origin". Journal of the Chemical Society, Chemical Communications (4): 147. doi:10.1039/C39730000147.

[Merck-1] Merck Index, 11th Edition, 3417

[2] Iimura, H; Takeuchi, T; Kondo, S; Matsuzaki, M; Umezawa, H (1972). "Dopastin, an inhibitor of dopamine -hydroxylase". The Journal of Antibiotics. 25 (8): 497–500. doi:10.7164/antibiotics.25.497. PMID 4648494.

[3] H. Iinuma; M. Matsuzaki; T. Nagatsu; T. Takeuchi; H. Umezawa (1974). "Biochemical and biological studies on dopastin, an inhibitor of dopamine β-hydroxylase". Agric. Biol. Chem. 38 (11): 2107–2111. doi:10.1271/bbb1961.38.2107.

[4] Ohno, M.; Iinuma, H.; Yagisawa, N.; Shibahara, S.; Suhara, Y.; Kondo, S.; Maeda, K.; Umezawa, H. (1973). "Synthesis of dopastin, a dopamine ?-hydroxylase inhibitor of microbial origin". Journal of the Chemical Society, Chemical Communications (4): 147. doi:10.1039/C39730000147.

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