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A-500359 M-1

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Category Antibiotics
Catalog number BBF-03180
CAS
Molecular Weight 635.66
Molecular Formula C23H33N5O12S2

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Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

A-500359 M-1 is a bacterial translocase-1 (Translocase I, EC 2.7. 8.13) inhibitor produced by Streptomyces griseus SANK 60196. It has activity against Mycobacterium smegmatis, Streptococcus pneumoniae and Streptococcus pyogenes, with an MIC of 6.25-12.5 µg/mL.

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Synonyms N-[2-({2-[(6-{[(2S,3S,4R,5R)-5-(2,4-Dioxo(1,3-dihydropyrimidinyl))-4-hydroxy-3-methoxyoxolan-2-yl]carbamoylmethoxy}(4S,5S,6S)-4,5-dihydroxy-4H-5,6-dihydropyran-2-yl)carbonylamino]ethyl}disulfanyl)ethyl]acetamide
IUPAC Name (2S,3S,4S)-N-[2-(2-acetamidoethyldisulfanyl)ethyl]-2-[(1R)-2-amino-1-[(2S,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-4-hydroxy-3-methoxyoxolan-2-yl]-2-oxoethoxy]-3,4-dihydroxy-3,4-dihydro-2H-pyran-6-carboxamide
Canonical SMILES CC(=O)NCCSSCCNC(=O)C1=CC(C(C(O1)OC(C2C(C(C(O2)N3C=CC(=O)NC3=O)O)OC)C(=O)N)O)O
InChI InChI=1S/C23H33N5O12S2/c1-10(29)25-4-7-41-42-8-5-26-20(35)12-9-11(30)14(32)22(38-12)40-18(19(24)34)17-16(37-2)15(33)21(39-17)28-6-3-13(31)27-23(28)36/h3,6,9,11,14-18,21-22,30,32-33H,4-5,7-8H2,1-2H3,(H2,24,34)(H,25,29)(H,26,35)(H,27,31,36)/t11-,14-,15+,16-,17-,18+,21+,22+/m0/s1
InChI Key ZUCKJVVXVVOESY-KQSVRIFWSA-N
Antibiotic Activity Spectrum Gram-positive bacteria; mycobacteria
Density 1.6±0.1 g/cm3
1. Studies on novel bacterial translocase I inhibitors, A-500359s. III. Deaminocaprolactam derivatives of capuramycin: A-500359 E, F, H; M-1 and M-2
Yasunori Muramatsu, Shunichi Miyakoshi, Yasumasa Ogawa, Takashi Ohnuki, Michiko Miyazawa Ishii, Masatoshi Arai, Toshio Takatsu, Masatoshi Inukai J Antibiot (Tokyo). 2003 Mar;56(3):259-67. doi: 10.7164/antibiotics.56.259.
Novel derivatives of capuramycin were obtained when 10 mM of 2-aminoethyl-L-cysteine (AEC), an inhibitor of aspartokinase, was added to the culture of Streptomyces griseus SANK 60196, the producer of A-500359. They were purified from the culture filtrate and their chemical structures were elucidated as a deaminocaprolactam derivative of capuramycin designated as A-500359 F, A-500359 E, a methyl ester of A-500359 F, and A-500359 H, a 3'-demethyl derivative of A-500359 F. Two other compounds, A-500359 M-1 and A-500359 M-2, were purified from the same medium and their structures were elucidated. A-500359 E, F, H, M-1 and M-2 inhibited bacterial translocase I with an IC50 of 0.027 microM, 1.1 microM, 0.008 microM, 0.058 microM and 0.010 microM, respectively. A-500359 E, M-1 and M-2 inhibited the growth of mycobacteria as well.

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