Alazopeptin

Alazopeptin
Clinical data
ATC code	None;
Identifiers
	IUPAC name 6-diazo-2-{6-diazo-5-oxo-2-[(prop-2-en-1-yl)amino]hexanamido}-5-oxohexanoic acid;
CAS Number	1397-84-8 ;
PubChem CID	5486654;
ChemSpider	16735646 ;
UNII	H2QL5CU7EQ;
ChEMBL	ChEMBL92957 ;
Chemical and physical data
Formula	C15H20N6O5
Molar mass	364.362 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C=CCNC(CCC(=C[N+]#N)[O-])C(=O)NC(CCC(=C[N+]#N)[O-])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 ;
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Alazopeptin is an antibiotic, with moderate anti-trypanosomal[1] and antitumor activity.[2] It was originally isolated from Streptomyces griseoplanus, sourced from soil near Williamsburg, Iowa.[3] It is still largely produced via fermentation broths of that organism.

References

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.
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.
Patterson EL, Johnson BL, DeVoe SE, Bohonos N (1965). "Structure of the antitumor antibiotic alazopeptin". Antimicrob Agents Chemother. 5: 115–8. PMID 5883414.

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[IshiyamaOtoguro2008-1] 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.

[HataUmezawa1973-2] 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.