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Dopastin

Dopastin
Names
Preferred IUPAC name
(2E)-N-{(2S)-2-[Hydroxy(nitroso)amino]-3-methylbutyl}but-2-enamide
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • 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
  • O=C(NC[C@@H](N(O)N=O)C(C)C)/C=C/C
Properties
C9H17N3O3
Molar mass 215.253 g·mol−1
Melting point 116 to 119 °C (241 to 246 °F; 389 to 392 K)[1]
Acidity (pKa) 5.1[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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

[edit]
  1. ^ a b 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.