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 ;
	(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

^ 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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[IshiyamaOtoguro2008-1] 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.

[HataUmezawa1973-2] 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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