Alazopeptin

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.[4] 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.[5][6] In 2021 the biosynthetic pathway of alazopeptin was elucidated.[7][8]

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)

References
  1. Ishiyama, Aki; Otoguro, Kazuhiko; Namatame, Miyuki; Nishihara, Aki; Furusawa, Toshiaki; Masuma, Rokuro; Shiomi, Kazuro; Takahashi, Yoko; Ichimura, Michio; Yamada, Haruki; Ōmura, Satoshi (2008). "In Vitro and in Vivo Antitrypanosomal Activitiy of Two Microbial Metabolites, KS-505a and Alazopeptin". The Journal of Antibiotics. 61 (10): 627–632. doi:10.1038/ja.2008.83. ISSN 0021-8820. PMID 19168977.
  2. Hata, Toju; Umezawa, Iwao; Iwai, Yuzuru; Katagiri, Mlchiko; Awaya, Juichi; Komiyama, Kanki; Oiwa, Ruiko; Atsumi, Kiyoo (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. ISSN 0021-8820. PMID 4205875.
  3. Patterson EL, Johnson BL, DeVoe SE, Bohonos N (1965). "Structure of the antitumor antibiotic alazopeptin". Antimicrob Agents Chemother. 5: 115–8. PMID 5883414.
  4. 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. ISSN 0021-8820. PMID 4205875.
  5. De Voe, S. E.; Rigler, N. E.; Shay, A. J.; Martin, J. H.; Boyd, T. C.; Backus, E. J.; Mowat, J. H.; Bohonos, N. (1956–1957). "Alazopeptin; production, isolation, and chemical characteristics". Antibiotics Annual: 730–735. ISSN 0570-3131. PMID 13425456.
  6. Patterson, E. L.; Johnson, B. L.; DeVoe, S. E.; Bohonos, N. (1965). "Structure of the antitumor antibiotic alazopeptin". Antimicrobial Agents and Chemotherapy. 5: 115–118. PMID 5883414.
  7. Kawai, Seiji; Sugaya, Yuko; Hagihara, Ryota; Tomita, Hiroya; Katsuyama, Yohei; Ohnishi, Yasuo (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 International Edition. 60 (18): 10319–10325. doi:10.1002/anie.202100462. ISSN 1521-3773. PMID 33624374. S2CID 232039107.
  8. Kawai, Seiji; Katsuyama, Yohei; Ohnishi, Yasuo (2022-02-21). "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. ISSN 1439-4227. PMID 35132756. S2CID 246651326.


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