Luminamicin
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| Category | Antibiotics |
| Catalog number | BBF-01043 |
| CAS | 99820-21-0 |
| Molecular Weight | 614.64 |
| Molecular Formula | C32H38O12 |
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Description
It is produced by the strain of Actinoplanes coloradoensis. It mainly inhibits the anaerobic bacteria, such as clostridium and clostridium, and has certain effects on haemophilus influenzae and Gonorrhoeae cuminella, but not against other aerobic bacteria.
Specification
| Synonyms | Coloradocin; 1,24-Methano-1H,9H,15H-furo(3',4':10,11)(1,7)dioxacyclotetradecino(4,3-e)pyrano(2,3-i)(4)benzoxecin-6,13,15,18(3ah)-tetrone,4,5,7a,8,16,17,20,20a,24,25,26,26a-dodecahydro-8,26-dihydroxy-22,25-dimethyl-5-methoxy- |
| IUPAC Name | (1S,2E,15E,20S,25S,28R,30R,31R,32R,33S)-19,32-dihydroxy-23-methoxy-2,31-dimethyl-6,12,17,21,34-pentaoxahexacyclo[28.3.1.01,25.04,20.010,14.028,33]tetratriaconta-2,10(14),15,26-tetraene-7,11,13,22-tetrone |
| Canonical SMILES | CC1C2CC3C=CC4CC(C(=O)OC5C(COC(=O)CCC6=C(C=COCC5O)C(=O)OC6=O)C=C(C4(C3C1O)O2)C)OC |
| InChI | InChI=1S/C32H38O12/c1-15-10-18-13-41-25(34)7-6-20-21(30(37)43-29(20)36)8-9-40-14-22(33)28(18)42-31(38)24(39-3)12-19-5-4-17-11-23-16(2)27(35)26(17)32(15,19)44-23/h4-5,8-10,16-19,22-24,26-28,33,35H,6-7,11-14H2,1-3H3/b9-8+,15-10+/t16-,17-,18?,19+,22?,23+,24?,26-,27+,28-,32-/m0/s1 |
| InChI Key | UGSGHHXIPUAOBJ-FUQUDWCDSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Solubility | Soluble in Acetonitrile |
Reference Reading
1. Pd-catalyzed Regio- and Stereoselective Hydrostannylation of an Alkyl Ethynyl Ether/One-Pot Stille Coupling Enables the Synthesis of 14-Membered Macrolactone of Luminamicin
Akihiro Sugawara, Hirokazu Takada, Tomoyasu Hirose, Aoi Kimishima, Takeshi Yamada, Masaki Toda, Toru Kojima, Takanori Matsumaru, Toshiaki Sunazuka Org Lett. 2021 Mar 5;23(5):1758-1763. doi: 10.1021/acs.orglett.1c00183. Epub 2021 Feb 16.
Regio- and stereoselective hydrostannylation of alkyl ethynyl ethers generates alkenyl ethers, which are useful building blocks in organic synthesis. This efficient synthetic method, however, is limited. Here, we report not only an efficient method for a highly regio- and stereoselective Pd-catalyzed hydrostannylation of alkyl ethynyl ethers but also a scalable synthesis and construction of the core framework of luminamicin possessing all functional groups and stereocenters.
2. Toward the total synthesis of luminamicin; an anaerobic antibiotic: construction of highly functionalized cis-decalin containing a bridged ether moiety
Hiroyasu Ando, Aoi Kimishima, Motoyoshi Ohara, Tomoyasu Hirose, Takanori Matsumaru, Hirokazu Takada, Keisuke Morodome, Takehiro Miyamoto, Akihiro Sugawara, Satoshi Ōmura, Toshiaki Sunazuka J Antibiot (Tokyo). 2018 Feb;71(2):268-272. doi: 10.1038/ja.2017.77. Epub 2017 Jul 5.
Synthesis of a cis-decalin moiety, containing an oxa-bridged cis-decalin ring system (11-oxatricyclo(5.3.1.1,703,8)undecane), as a key intermediate of the total synthesis of luminamicin (1) was accomplished. One of the essential steps in our synthetic route is construction of a cis-decaline framework using a one-pot Michael addition-aldol reaction. Additionally, the bridged ether moiety was obtained by an intramolecular 1,6-oxa-Michael reaction of a conjugated aldehyde.
3. Chemical Degradation-Inspired Total Synthesis of the Antibiotic Macrodiolide, Luminamicin
Aoi Kimishima, Hiroyasu Ando, Goh Sennari, Yoshihiko Noguchi, Shogo Sekikawa, Toru Kojima, Motoyoshi Ohara, Yoshihiro Watanabe, Yuki Inahashi, Hirokazu Takada, Akihiro Sugawara, Takanori Matsumaru, Masato Iwatsuki, Tomoyasu Hirose, Toshiaki Sunazuka J Am Chem Soc. 2022 Dec 21;144(50):23148-23157. doi: 10.1021/jacs.2c10856. Epub 2022 Dec 9.
This article describes the first total synthesis of luminamicin using a strategy combining chemical degradation with synthesis. Chemical degradation studies provided a sense of the inherent reactivity of the natural product, and deconstruction of the molecule gave rise to a key intermediate, which became the target for chemical synthesis. The core structure of the southern part of luminamicin was constructed by a 1,6-oxa-Michael reaction to form an oxa-bridged ring, followed by coupling with a functionalized organolithium species. Modified Shiina macrolactonization conditions forged the strained 10-membered lactone containing a tri-substituted olefin. Diastereoselective α-oxidation of the 10-membered lactone completed the center part to provide the key intermediate. Inspired by the degradation study, an unprecedented enol ether/maleic anhydride moiety was constructed with a one-pot chlorosulfide coupling and thiol β-elimination sequence. Finally, macrolactonization to the 14-membered ring in the presence of the highly electrophilic maleic anhydride moiety was accomplished using modified Mukaiyama reagents to complete the synthesis of luminamicin.
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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 ╳
