Alazopeptin

Last updated
Alazopeptin
Alazopeptin Structure.svg
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
Formula C15H20N6O5
Molar mass 364.362 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- X mark.svgN
  • Key:RCQIFJCPIWRTAF-WGEIWTTOSA-N X mark.svgN
 X mark.svgNYes check.svgY  (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

  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. 1 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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