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Alazopeptin

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Chemical compound Pharmaceutical compound
Alazopeptin
Clinical data
ATC code
  • None
Identifiers
IUPAC name
  • 6-diazo-2-{6-diazo-5-oxo-2-hexanamido}-5-oxohexanoic acid
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC15H20N6O5
Molar mass364.362 g·mol
3D model (JSmol)
SMILES
  • C=CCNC(CCC(=C#N))C(=O)NC(CCC(=C#N))C(=O)O
InChI
  • 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-
  • Key:RCQIFJCPIWRTAF-WGEIWTTOSA-N
  (what is this?)  (verify)

Alazopeptin is an antibiotic, with moderate anti-trypanosomal and antitumor activity. It was originally isolated from Streptacidiphilus griseoplanus, sourced from soil near Williamsburg, Iowa. It is also isolated from Kitasatospora azatica 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. In 2021 the biosynthetic pathway of alazopeptin was elucidated.

References

  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.
  2. ^ 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.
  3. Patterson EL, Johnson BL, DeVoe SE, Bohonos N (1965). "Structure of the antitumor antibiotic alazopeptin". Antimicrobial Agents and Chemotherapy. 5: 115–118. PMID 5883414.
  4. 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.
  5. Patterson EL, Johnson BL, DeVoe SE, Bohonos N (1965). "Structure of the antitumor antibiotic alazopeptin". Antimicrobial Agents and Chemotherapy. 5: 115–118. PMID 5883414.
  6. 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.
  7. 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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