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Inosamycin A

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Inosamycin A
Category Antibiotics
Catalog number BBF-01503
CAS 91421-97-5
Molecular Weight 615.63
Molecular Formula C23H45N5O14

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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

Inosamycin A is a broad-spectrum antimicrobial antibiotic originally isolated from Str. hygroscopicus No. J296-21. Its antibacterial activity was comparable to that of neomycin, and about twice that of ribomycin.

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Synonyms Bu 2659A; 6-Amino-2-{[3-O-(2,6-diamino-2,6-dideoxyhexopyranosyl)pentofuranosyl]oxy}-3,4-dihydroxycyclohexyl 2,6-diamino-2,6-dideoxyhexopyranoside
IUPAC Name (2R,3S,4R,5R,6R)-5-amino-6-[(1R,2R,3S,4R,6S)-6-amino-2-[(2S,3R,4S,5R)-4-[(2R,3S,4S,5R,6R)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-3,4-dihydroxycyclohexyl]oxy-2-(aminomethyl)oxane-3,4-diol
Canonical SMILES C1C(C(C(C(C1O)O)OC2C(C(C(O2)CO)OC3C(C(C(C(O3)CN)O)O)N)O)OC4C(C(C(C(O4)CN)O)O)N)N
InChI InChI=1S/C23H45N5O14/c24-2-7-13(32)15(34)10(27)21(37-7)40-18-5(26)1-6(30)12(31)20(18)42-23-17(36)19(9(4-29)39-23)41-22-11(28)16(35)14(33)8(3-25)38-22/h5-23,29-36H,1-4,24-28H2/t5-,6+,7+,8+,9+,10+,11-,12-,13+,14-,15+,16-,17+,18+,19+,20+,21+,22+,23-/m0/s1
InChI Key HNBFTXDNUFWYJV-MXESDJFFSA-N
Appearance White Amorphous Solid
Boiling Point 923.7°C at 760 mmHg
Melting Point 210-215°C
Density 1.64 g/cm3
1. Inosamycin, a complex of new aminoglycoside antibiotics. I. Production, isolation and properties
M Tsunakawa, M Hanada, H Tsukiura, K Tomita, K Tomatsu, T Hoshiya, T Miyaki, M Konishi, H Kawaguchi J Antibiot (Tokyo). 1985 Oct;38(10):1302-12. doi: 10.7164/antibiotics.38.1302.
A strain of Streptomyces hygroscopicus No. J296-21 (ATCC 39150) was found to produce a complex of new antibiotics, called inosamycins, which consisted of components A, B, C, D and E. They are novel aminocyclitol antibiotics structurally related to neomycin, paromomycin and ribostamycin. The antibiotic complex and each component of inosamycin exhibit a broad antibacterial spectrum but they are inactive against most of the aminoglycoside-resistant organisms. The antibacterial activity of inosamycin A, the major component of the complex, is comparable to that of neomycin but its acute toxicity is significantly lower (ca. 1/3) than that of neomycin.
2. Inosamycin, a complex of new aminoglycoside antibiotics. II. Structure determination
M Tsunakawa, M Hanada, H Tsukiura, M Konishi, H Kawaguchi J Antibiot (Tokyo). 1985 Oct;38(10):1313-21. doi: 10.7164/antibiotics.38.1313.
Structures of the new aminocyclitol antibiotics, inosamycins A, B, C, D and E, have been determined by a combination of chemical degradation and spectroscopic studies. They are structurally related to neomycin, paromomycin and ribostamycin but differ in that all the inosamycin components contain 2-deoxy-scyllo-inosamine in place of 2-deoxystreptamine in the known aminoglycoside antibiotics.

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