丙氨肽素

丙氨肽素
臨床資料
ATC碼	未分配;
识别信息
	IUPAC命名法 6-diazo-26-diazo-5-oxo-2-[(prop-2-en-1-yl)amino]hexanamido5-oxohexanoic acid; ;
CAS号	1397-84-8 [NIH]
PubChem CID	5486654;
ChemSpider	16735646 ;
UNII	H2QL5CU7EQ;
ChEMBL	ChEMBL92957 ;
化学信息
化学式	C15H20N6O5
摩尔质量	364.36 g·mol−1
3D模型（JSmol（英语：JSmol））	交互式图像;
	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 ;

丙氨肽素（英語：Alazopeptin）是一种抗生素，具有中等抗锥虫^[1]和抗肿瘤活性。^[2]它最初是从来自爱荷华州威廉斯堡附近的土壤中的Streptacidiphilus griseoplanus（英语：Streptacidiphilus griseoplanus）中分离出来的。^[3]它也可以从Kitasatospora azatica中分离出来。^[2]它仍然主要通过该生物体的发酵液产生。从结构上来看，丙氨肽素是一种三肽，含有2个6-重氮-5-氧代-L-正亮氨酸（英语：6-Diazo-5-oxo-L-norleucine）分子和1个L-丙氨酸分子。^[4]^[5]2021年，丙氨肽素的生物合成途径被详细描述。^[6]^[7]

参考资料

^ Ishiyama A, Otoguro K, Namatame M, Nishihara A, Furusawa T, Masuma R, et al. In vitro and in vivo antitrypanosomal activitiy [sic] of two microbial metabolites, KS-505a and alazopeptin. The Journal of Antibiotics. October 2008, 61 (10): 627–632. PMID 19168977. doi:10.1038/ja.2008.83  .
^ ^2.0 ^2.1 Hata T, Umezawa I, Iwai Y, Katagiri M, Awaya J. Studies on the antitumor activity of an alazopeptin isolated from a new strain of Streptomyces. The Journal of Antibiotics. March 1973, 26 (3): 181–183. PMID 4205875. doi:10.7164/antibiotics.26.181  .
^ Patterson EL, Johnson BL, DeVoe SE, Bohonos N. Structure of the antitumor antibiotic alazopeptin. Antimicrobial Agents and Chemotherapy. 1965, 5: 115–118. PMID 5883414.
^ De Voe SE, Rigler NE, Shay AJ, Martin JH, Boyd TC, Backus EJ, et al. Alazopeptin; production, isolation, and chemical characteristics. Antibiotics Annual. 1956–1957: 730–735 [2024-04-19]. PMID 13425456. （原始内容存档于2024-04-19）.
^ Patterson EL, Johnson BL, DeVoe SE, Bohonos N. Structure of the antitumor antibiotic alazopeptin. Antimicrobial Agents and Chemotherapy. 1965, 5: 115–118 [2024-04-19]. PMID 5883414. （原始内容存档于2024-04-19）.
^ Kawai S, Sugaya Y, Hagihara R, Tomita H, Katsuyama Y, Ohnishi Y. 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. April 2021, 60 (18): 10319–10325. PMID 33624374. S2CID 232039107. doi:10.1002/anie.202100462.
^ Kawai S, Katsuyama Y, Ohnishi Y. The α/β Hydrolase AzpM Catalyzes Dipeptide Synthesis in Alazopeptin Biosynthesis Using Two Molecules of Carrier Protein-Tethered Amino Acid. ChemBioChem. April 2022, 23 (7): e202100700. PMID 35132756. S2CID 246651326. doi:10.1002/cbic.202100700.

[IshiyamaOtoguro2008-1] Ishiyama A, Otoguro K, Namatame M, Nishihara A, Furusawa T, Masuma R, et al. In vitro and in vivo antitrypanosomal activitiy [sic] of two microbial metabolites, KS-505a and alazopeptin. The Journal of Antibiotics. October 2008, 61 (10): 627–632. PMID 19168977. doi:10.1038/ja.2008.83  .

[HataUmezawa1973-2] 2.0 ^2.1 Hata T, Umezawa I, Iwai Y, Katagiri M, Awaya J. Studies on the antitumor activity of an alazopeptin isolated from a new strain of Streptomyces. The Journal of Antibiotics. March 1973, 26 (3): 181–183. PMID 4205875. doi:10.7164/antibiotics.26.181  .

[3] Patterson EL, Johnson BL, DeVoe SE, Bohonos N. Structure of the antitumor antibiotic alazopeptin. Antimicrobial Agents and Chemotherapy. 1965, 5: 115–118. PMID 5883414.

[4] De Voe SE, Rigler NE, Shay AJ, Martin JH, Boyd TC, Backus EJ, et al. Alazopeptin; production, isolation, and chemical characteristics. Antibiotics Annual. 1956–1957: 730–735 [2024-04-19]. PMID 13425456. （原始内容存档于2024-04-19）.

[5] Patterson EL, Johnson BL, DeVoe SE, Bohonos N. Structure of the antitumor antibiotic alazopeptin. Antimicrobial Agents and Chemotherapy. 1965, 5: 115–118 [2024-04-19]. PMID 5883414. （原始内容存档于2024-04-19）.

[6] Kawai S, Sugaya Y, Hagihara R, Tomita H, Katsuyama Y, Ohnishi Y. 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. April 2021, 60 (18): 10319–10325. PMID 33624374. S2CID 232039107. doi:10.1002/anie.202100462.

[7] Kawai S, Katsuyama Y, Ohnishi Y. The α/β Hydrolase AzpM Catalyzes Dipeptide Synthesis in Alazopeptin Biosynthesis Using Two Molecules of Carrier Protein-Tethered Amino Acid. ChemBioChem. April 2022, 23 (7): e202100700. PMID 35132756. S2CID 246651326. doi:10.1002/cbic.202100700.

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臨床資料

ATC碼	未分配
识别信息
IUPAC命名法 6-diazo-26-diazo-5-oxo-2-[(prop-2-en-1-yl)amino]hexanamido5-oxohexanoic acid
CAS号	1397-84-8 ^Y[NIH]
PubChem CID	5486654
ChemSpider	16735646^N
UNII	H2QL5CU7EQ
ChEMBL	ChEMBL92957^N
化学信息
化学式	C₁₅H₂₀N₆O₅
摩尔质量	364.36 g·mol⁻¹
3D模型（JSmol（英语：JSmol））	交互式图像
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-^N Key:RCQIFJCPIWRTAF-WGEIWTTOSA-N^N