Crisamicin A
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| Category | Antibiotics |
| Catalog number | BBF-01076 |
| CAS | 95828-47-0 |
| Molecular Weight | 598.51 |
| Molecular Formula | C32H22O12 |
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Description
It is produced by the strain of Micromonospora purpureochromogenes subsp. lalotolerans. It only has activity against gram-positive bacteria. The activity of samicin C is stronger than Crisamicin A.
Specification
| Synonyms | (3aS)-5β,5'β-Dimethyl-10,10'-dihydroxy-3,3',3aβ,3'aβ,5,5',6,6',11,11',11bβ,11'bβ-dodecahydro-8,8'-bi[2H-furo[3,2-b]naphtho[2,3-d]pyran]-2,2',6,6',11,11'-hexaone; (3aS,3'aS,5S,5'S,11bS,11'bS)-3,3',3a,3'a,5,5',11b,11'b-Octahydro-10,10'-dihydroxy-5,5'-dimethyl-8,8'-bi[2H-furo[3,2-b]naphtho[2,3-d]pyran]-2,2',6,6',11,11'-hexone; CRS-A; (8,8'-Bi-2H-furo(3,2-b)naphtho(2,3-d)pyran)-2,2',6,6'11,11'-hexone,3,3',3a,3'a,5,5',11b,11'b-octahydro-10,10'-dihydroxy-5,5'-dimethyl-, (3aS-(3aalpha,5alpha,8(3aR*,5R*,11bR*),11balpha))- |
| IUPAC Name | (11S,15S,17S)-7-hydroxy-5-[(11S,15S,17S)-7-hydroxy-17-methyl-2,9,13-trioxo-12,16-dioxatetracyclo[8.7.0.03,8.011,15]heptadeca-1(10),3(8),4,6-tetraen-5-yl]-17-methyl-12,16-dioxatetracyclo[8.7.0.03,8.011,15]heptadeca-1(10),3(8),4,6-tetraene-2,9,13-trione |
| Canonical SMILES | CC1C2=C(C3C(O1)CC(=O)O3)C(=O)C4=C(C2=O)C=C(C=C4O)C5=CC6=C(C(=C5)O)C(=O)C7=C(C6=O)C(OC8C7OC(=O)C8)C |
| InChI | InChI=1S/C32H22O12/c1-9-21-25(31-17(41-9)7-19(35)43-31)29(39)23-13(27(21)37)3-11(5-15(23)33)12-4-14-24(16(34)6-12)30(40)26-22(28(14)38)10(2)42-18-8-20(36)44-32(18)26/h3-6,9-10,17-18,31-34H,7-8H2,1-2H3/t9-,10-,17-,18-,31+,32+/m0/s1 |
| InChI Key | IPAXVRZEFNMCLP-GJPLRXPFSA-N |
Properties
| Appearance | Orange Acicular Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Solubility | Soluble in Chloroform, Methanol |
Reference Reading
1. Synthetic studies on actinorhodin and γ-actinorhodin: synthesis of deoxyactinorhodin and deoxy-γ-actinorhodin/crisamicin A isomer
Sandip V Mulay, Rodney A Fernandes Chemistry. 2015 Mar 16;21(12):4842-52. doi: 10.1002/chem.201406431. Epub 2015 Feb 11.
A strategy based on bidirectional Dötz benzannulation and the oxa-Pictet-Spengler reaction toward the synthesis of actinorhodin and γ-actinorhodin has been explored. This work has resulted in the synthesis of deoxyactinorhodin and deoxy-γ-actinorhodin. The latter is a regioisomer of crisamicin A (which has 10,10'-dihydroxy groups).
2. Stereoselective Total Synthesis of the Dimeric Naphthoquinonopyrano-γ-lactone (-)-Crisamicin A: Introducing the Dimerization Site by a Late-Stage Hartwig Borylation
Julia Kopp, Reinhard Brückner Org Lett. 2020 May 1;22(9):3607-3612. doi: 10.1021/acs.orglett.0c01078. Epub 2020 Apr 16.
The first stereoselective total synthesis of the dimeric naphthoquinonopyrano-γ-lactone (-)-crisamicin A was realized (13 steps, 5% overall yield). 1,4,5-Trimethoxynaphthalene, reached in five known steps, was brominated at C-3 to install a but-3-enoic ester by an ensuing Heck coupling. An asymmetric Sharpless dihydroxylation followed and gave a β-hydroxy-γ-lactone with >99.9% ee. Its OH substituent and acetaldehyde established the dihydropyran ring in a completely diastereoselective oxa-Pictet-Spengler cyclization. The 2,3-fused anisole moiety allowed the C5-H bond under Hartwig's conditions to be borylated. This set the stage for engaging the resulting C5-B bond in an oxidative dimerization, which led to a binaphthohydroquinon-5-yl. The latter was advanced to synthetic crisamicin A by a double CAN oxidation (→ a binaphthoquinon-5-yl) and a double demethylation.
3. Toward an asymmetric synthesis of the dimeric pyranonaphthoquinone antibiotic crisamicin A
Margaret A Brimble, Najmah P S Hassan, Briar J Naysmith, Jonathan Sperry J Org Chem. 2014 Aug 1;79(15):7169-78. doi: 10.1021/jo501344c. Epub 2014 Jul 23.
A full account of our efforts toward an asymmetric synthesis of crisamicin A are presented. The key steps include a Hauser-Kraus annulation of a cyanophthalide with a chiral enone-lactone, a stereoselective cyclization-reduction to install the pyran unit, and a Suzuki homocoupling to forge the key biaryl bond. This work has culminated in the asymmetric synthesis of a dimer bearing the complete carbon skeleton of the dimeric pyranonaphthoquinone natural product crisamicin A.
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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 ╳
