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1 References  













Alazopeptin






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From Wikipedia, the free encyclopedia
  

Alazopeptin
Clinical data
ATC code
  • None
Identifiers

  • 6-diazo-2-{6-diazo-5-oxo-2-[(prop-2-en-1-yl)amino]hexanamido}-5-oxohexanoic acid

CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC15H20N6O5
Molar mass364.362 g·mol−1
3D model (JSmol)

  • C=CCNC(CCC(=C[N+]#N)[O-])C(=O)NC(CCC(=C[N+]#N)[O-])C(=O)O

  • InChI=1S/C15H20N6O5/c1-2-7-18-12(5-3-10(22)8-19-16)14(24)21-13(15(25)26)6-4-11(23)9-20-17/h2,8-9,12-13,18H,1,3-7H2,(H2-2,21,22,23,24,25,26)/b10-8-,11-9- ☒N

  • Key:RCQIFJCPIWRTAF-WGEIWTTOSA-N ☒N

 ☒NcheckY (what is this?)  (verify)

Alazopeptin is an antibiotic, with moderate anti-trypanosomal[1] and antitumor activity.[2] It was originally isolated from Streptacidiphilus griseoplanus, sourced from soil near Williamsburg, Iowa.[3] It is also isolated from Kitasatospora azatica[2] It is still largely produced via fermentation broths of that organism. Structurally, alazopeptin is a tripeptide and contains 2 molecules of 6-diazo-5-oxo-L-norleucine and one molecule of L-alanine.[4][5] In 2021 the biosynthetic pathway of alazopeptin was elucidated.[6][7]

References

[edit]
  1. ^ Ishiyama A, Otoguro K, Namatame M, Nishihara A, Furusawa T, Masuma R, et al. (October 2008). "In vitro and in vivo antitrypanosomal activitiy [sic] of two microbial metabolites, KS-505a and alazopeptin". The Journal of Antibiotics. 61 (10): 627–632. doi:10.1038/ja.2008.83. PMID 19168977.
  • ^ a b Hata T, Umezawa I, Iwai Y, Katagiri M, Awaya J (March 1973). "Studies on the antitumor activity of an alazopeptin isolated from a new strain of Streptomyces". The Journal of Antibiotics. 26 (3): 181–183. doi:10.7164/antibiotics.26.181. PMID 4205875.
  • ^ Patterson EL, Johnson BL, DeVoe SE, Bohonos N (1965). "Structure of the antitumor antibiotic alazopeptin". Antimicrobial Agents and Chemotherapy. 5: 115–118. PMID 5883414.
  • ^ De Voe SE, Rigler NE, Shay AJ, Martin JH, Boyd TC, Backus EJ, et al. (1956–1957). "Alazopeptin; production, isolation, and chemical characteristics". Antibiotics Annual: 730–735. PMID 13425456.
  • ^ Patterson EL, Johnson BL, DeVoe SE, Bohonos N (1965). "Structure of the antitumor antibiotic alazopeptin". Antimicrobial Agents and Chemotherapy. 5: 115–118. PMID 5883414.
  • ^ Kawai S, Sugaya Y, Hagihara R, Tomita H, Katsuyama Y, Ohnishi Y (April 2021). "Complete Biosynthetic Pathway of Alazopeptin, a Tripeptide Consisting of Two Molecules of 6-Diazo-5-oxo-l-norleucine and One Molecule of Alanine". Angewandte Chemie. 60 (18): 10319–10325. doi:10.1002/anie.202100462. PMID 33624374. S2CID 232039107.
  • ^ Kawai S, Katsuyama Y, Ohnishi Y (April 2022). "The α/β Hydrolase AzpM Catalyzes Dipeptide Synthesis in Alazopeptin Biosynthesis Using Two Molecules of Carrier Protein-Tethered Amino Acid". ChemBioChem. 23 (7): e202100700. doi:10.1002/cbic.202100700. PMID 35132756. S2CID 246651326.
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    • Retrieved from "https://en.wikipedia.org/w/index.php?title=Alazopeptin&oldid=1222660285"
    Categories: 
    ●Drugs not assigned an ATC code
     ●Antibiotics
     ●Allylamines
     ●Diazo compounds
     ●Tripeptides
     ●Antineoplastic and immunomodulating drug stubs
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