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Antibiotic 66-40C

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Category Antibiotics
Catalog number BBF-02993
CAS 60870-21-5
Molecular Weight 856.96
Molecular Formula C38H64N8O14

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Fermentation Lab

4 R&D and scale-up labs

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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

It is a dimeric aminoglycoside antibiotic produced by the strain of Micromonospora inyoensis.

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Synonyms beta-L-Arabinopyranoside, 2,7,14,19-tetraamino-2,3,4,4a,7,8,12a,13,14,15,16,16a,18,19,20,24a-hexadecahydro-4,16-dihydroxy-6,10:18,22-diepoxy-1H,6H-dibenzo(b,l)(1,11,4,14)dioxadiazacycloeicosine-3,15-diylbis(3-deoxy-4-C-methyl-3-(methylamino)-, (2R-(2R*,3S*,4R*,4aR*,6S*,7R*,12aS*,14R*,15S*,16R*,16aR*,18S*,19R*,24aS*))-; Aminoglycoside 66-40-C
IUPAC Name (1R,3S,4S,5R,6S,8R,14R,15S,17R,18R,19S,20R,22S,28S)-6,14,20,28-tetraamino-5,19-bis[[(2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(methylamino)oxan-2-yl]oxy]-2,16,29,30-tetraoxa-9,23-diazapentacyclo[23.3.1.111,15.03,8.017,22]triaconta-9,11,23,25-tetraene-4,18-diol
Canonical SMILES CC1(COC(C(C1NC)O)OC2C(CC3C(C2O)OC4C(CC=C(O4)C=NC5CC(C(C(C5OC6C(CC=C(O6)C=N3)N)O)OC7C(C(C(CO7)(C)O)NC)O)N)N)N)O
InChI InChI=1S/C38H64N8O14/c1-37(51)13-53-35(25(49)31(37)43-3)57-27-19(41)9-21-29(23(27)47)59-33-17(39)7-5-16(55-33)12-46-22-10-20(42)28(58-36-26(50)32(44-4)38(2,52)14-54-36)24(48)30(22)60-34-18(40)8-6-15(56-34)11-45-21/h5-6,11-12,17-36,43-44,47-52H,7-10,13-14,39-42H2,1-4H3/t17-,18+,19-,20+,21+,22-,23-,24+,25-,26-,27+,28-,29-,30+,31-,32-,33-,34+,35-,36-,37+,38+/m1/s1
InChI Key OKDBJIDCKFMJCC-LCUGQODWSA-N
Appearance Amorphous Powder
Boiling Point 1109.1°C at 760 mmHg
Melting Point 185-205°C
Density 1.74 g/cm3
Solubility Soluble in Water, Methanol
1. Biomimetic synthesis and structural refinement of the macrocyclic dimer aminoglycoside 66-40C--the remarkably selective self-condensation of a putative aldehyde intermediate in the submerged culture medium producing sisomicin
Stephen Hanessian, Juan Pablo Maianti Chem Commun (Camb). 2010 Mar 28;46(12):2013-5. doi: 10.1039/b925668g. Epub 2010 Feb 15.
Aminoglycoside 66-40C, an unprecedented 16-membered bis-azadiene macrocyclic natural product isolated from the Micromonospora producer of the antibiotic sisomicin, was synthesized following a biomimetic strategy which definitively established its origin as arising from a remarkably selective non-enzymatic macro-dimerization.
2. Semisynthetic aminoglycoside antibacterials. 6. Synthesis of sisomicin, Antibiotic G-52, and novel 6'-substituted analogues of sisomicin from aminoglycoside 66-40C
D H Davies, A K Mallams, M Counelis, D Loebenberg, E L Moss Jr, J A Waitz J Med Chem. 1978 Feb;21(2):189-93. doi: 10.1021/jm00200a009.
The discovery of aminoglycoside 66-40C, a novel dimeric, unsaturated imine produced by Micromonospora inyoensis, afforded a versatile intermediate for the synthesis of a variety of sisomicin analogues modified at the 6' position. The conversion of 66-40C into sisomicin, antibiotic G-52, and a series of novel 6'-substituted analogues of sisomicin is described, and the biological activity of the products is discussed.

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Antibiotic 66-40C

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