Everninomicin B
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| Category | Antibiotics |
| Catalog number | BBF-00885 |
| CAS | 53296-30-3 |
| Molecular Weight | 1553.38 |
| Molecular Formula | C66H99Cl2NO36 |
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Description
Everninomicin B is a carbohydrate antibiotic produced by Micromonospora carbonacea var. carbonacea. It has anti-gram-positive bacteria and mycobacterial activity.
Specification
| Synonyms | Everninomycin-B; R-451-B |
| IUPAC Name | [6-[4',7-dihydroxy-6-[3-hydroxy-2-[4-hydroxy-6-[7'-hydroxy-7-methoxy-7'-(1-methoxyethyl)spiro[4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-2,4'-6,7a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyran]-6-yl]oxy-5-methoxy-2-(methoxymethyl)oxan-3-yl]oxy-5-methoxy-6-methyloxan-4-yl]oxy-2',4,7a-trimethylspiro[3a,4,6,7-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2,6'-oxane]-3'-yl]oxy-4-(5-methoxy-4,6-dimethyl-4-nitrooxan-2-yl)oxy-2-methyloxan-3-yl] 3,5-dichloro-4-hydroxy-2-methoxy-6-methylbenzoate |
| Canonical SMILES | CC1C(C(CC(O1)OC2C(OC3(CC2O)OC4C(OC(C(C4(O3)C)O)OC5C(C(OC(C5OC)C)OC6C(OC(C(C6O)OC)OC7C(C8C(CO7)OC9(O8)C1C(C(CO9)(C(C)OC)O)OCO1)OC)COC)O)C)C)OC1CC(C(C(O1)C)OC)(C)[N+](=O)[O-])OC(=O)C1=C(C(=C(C(=C1OC)Cl)O)Cl)C |
| InChI | InChI=1S/C66H99Cl2NO36/c1-24-37(48(82-13)39(68)40(71)38(24)67)57(75)97-44-25(2)90-35(17-32(44)94-36-19-62(8,69(77)78)53(85-16)28(5)91-36)96-43-27(4)101-65(18-31(43)70)104-54-29(6)93-61(52(74)63(54,9)105-65)99-49-42(73)58(92-26(3)45(49)81-12)98-46-33(20-79-10)95-60(50(83-14)41(46)72)100-59-51(84-15)47-34(21-86-59)102-66(103-47)56-55(87-23-88-56)64(76,22-89-66)30(7)80-11/h25-36,41-47,49-56,58-61,70-74,76H,17-23H2,1-16H3 |
| InChI Key | ZFRCWSCZDCAGAJ-UHFFFAOYSA-N |
Properties
| Appearance | White Crystals |
| Antibiotic Activity Spectrum | Gram-positive bacteria; mycobacteria |
| Melting Point | 184-185°C |
| Solubility | Soluble in Methanol, Chloroform, bases |
Reference Reading
1. Efficacy of an evernimicin (SCH27899) in vitro and in an animal model of Lyme disease
C S Pavia, G P Wormser, J Nowakowski, A Cacciapuoti Antimicrob Agents Chemother. 2001 Mar;45(3):936-7. doi: 10.1128/AAC.45.3.936-937.2001.
The MICs of evernimicin at which 90% of Borrelia burgdorferi patient isolates were inhibited ranged from 0.1 to 0.5 microg/ml. Evernimicin was as effective as ceftriaxone against B. burgdorferi in a murine model of experimental Lyme disease. As assessed by culturing the urinary bladders of infected C3H mice, no live Borrelia isolates were recoverable following antibiotic treatment.
2. Oxidative cyclizations in orthosomycin biosynthesis expand the known chemistry of an oxygenase superfamily
Kathryn M McCulloch, Emilianne K McCranie, Jarrod A Smith, Maruf Sarwar, Jeannette L Mathieu, Bryan L Gitschlag, Yu Du, Brian O Bachmann, T M Iverson Proc Natl Acad Sci U S A. 2015 Sep 15;112(37):11547-52. doi: 10.1073/pnas.1500964112. Epub 2015 Aug 3.
Orthosomycins are oligosaccharide antibiotics that include avilamycin, everninomicin, and hygromycin B and are hallmarked by a rigidifying interglycosidic spirocyclic ortho-δ-lactone (orthoester) linkage between at least one pair of carbohydrates. A subset of orthosomycins additionally contain a carbohydrate capped by a methylenedioxy bridge. The orthoester linkage is necessary for antibiotic activity but rarely observed in natural products. Orthoester linkage and methylenedioxy bridge biosynthesis require similar oxidative cyclizations adjacent to a sugar ring. We have identified a conserved group of nonheme iron, α-ketoglutarate-dependent oxygenases likely responsible for this chemistry. High-resolution crystal structures of the EvdO1 and EvdO2 oxygenases of everninomicin biosynthesis, the AviO1 oxygenase of avilamycin biosynthesis, and HygX of hygromycin B biosynthesis show how these enzymes accommodate large substrates, a challenge that requires a variation in metal coordination in HygX. Excitingly, the ternary complex of HygX with cosubstrate α-ketoglutarate and putative product hygromycin B identified an orientation of one glycosidic linkage of hygromycin B consistent with metal-catalyzed hydrogen atom abstraction from substrate. These structural results are complemented by gene disruption of the oxygenases evdO1 and evdMO1 from the everninomicin biosynthetic cluster, which demonstrate that functional oxygenase activity is critical for antibiotic production. Our data therefore support a role for these enzymes in the production of key features of the orthosomycin antibiotics.
3. Total synthesis of everninomicin 13,384-1--Part 1: retrosynthetic analysis and synthesis of the A1B(A)C fragment
K C Nicolaou, R M Rodríguez, H J Mitchell, H Suzuki, K C Fylaktakidou, O Baudoin, F L van Delft Chemistry. 2000 Sep 1;6(17):3095-115. doi: 10.1002/1521-3765(20000901)6:173.0.co;2-4.
In this first of a series of four articles we introduce everninomicin 13,384-1 (1), a powerful antibiotic effective against drug resistant bacteria, as a target for total synthesis and discuss its retrosynthetic analysis. From the three defined fragments required for the synthesis (2: A1B(A)C fragment; 4: DE fragment; 5: FGHA2 fragment), we describe herein two approaches to the A1B(A)C block. The first strategy relied on an olefin metathesis reaction to construct a common intermediate for rings B and C, but was faced with final protecting group problems. The second, and successful approach, involved a 1,2-phenylsulfeno migration and a sulfur directed glycosidation procedure to link rings B and C, as well as an acyl fluoride intermediate to install the sterically hindered aryl ester moiety (ring A1). The final stages of the synthesis of the required 2-phenylseleno glycosyl fluoride 2 required introduction of a phenylseleno group at C-1 of ring C followed by a novel, DAST-promoted 1,2-migration to produce the desired 2-beta-phenylseleno glycosyl fluoride moiety.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
