Macquarimicin B
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| Category | Antibiotics |
| Catalog number | BBF-02287 |
| CAS | 165561-13-7 |
| Molecular Weight | 388.45 |
| Molecular Formula | C22H28O6 |
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Description
It is produced by the strain of Micromonospora chalcea. It's an antibiotic.
Specification
| Synonyms | 3H-5,2-Ethanylylideneindeno[4,5-e]oxecin-3,11(1H)-dione,5,6,7,8,8a,10a,12,13,13a,13b-decahydro-7,15-dihydroxy-12-methyl-1-(2-oxopropyl)-, (1S,5R,7R,8aS,10aS,12R,13aR,13bS)-; 3H-5,2-Ethanylylideneindeno[4,5-e]oxecin-3,11(1H)-dione,5,6,7,8,8a,10a,12,13,13a,13b-decahydro-7,15-dihydroxy-12-methyl-1-(2-oxopropyl)-, [1S-(1R*,5S*,7S*,8aR*,10aR*,12S*,13aS*,13bR*)]-; 1H-2,5-Ethanoindeno[4,5-e]oxecin-3,11-dione,5,6,7,8,8a,10a,12,13,13a,13b-decahydro-7,15-dihydroxy-12-methyl-1-(2-oxopropyl)-, (1S,5R,7R,8aS,10aS,12R,13aR,13bS)- |
| IUPAC Name | (2S,3S,4R,6R,8S,11S,13R,15R)-13,18-dihydroxy-6-methyl-2-(2-oxopropyl)-16-oxatetracyclo[13.2.2.03,11.04,8]nonadeca-1(18),9-diene-7,17-dione |
| Canonical SMILES | CC1CC2C(C1=O)C=CC3C2C(C4=C(CC(CC(C3)O)OC4=O)O)CC(=O)C |
| InChI | InChI=1S/C22H28O6/c1-10-5-16-15(21(10)26)4-3-12-7-13(24)8-14-9-18(25)20(22(27)28-14)17(19(12)16)6-11(2)23/h3-4,10,12-17,19,24-25H,5-9H2,1-2H3/t10-,12-,13-,14-,15+,16+,17+,19+/m1/s1 |
| InChI Key | MLTKAVZDJLQPHH-OKLWPZDHSA-N |
Properties
| Appearance | Crystal |
| Solubility | Soluble in Ethanol |
Reference Reading
1. Total synthesis of macquarimicins using an intramolecular Diels-Alder approach inspired by a biosynthetic pathway
Ryosuke Munakata, Hironori Katakai, Tatsuo Ueki, Jun Kurosaka, Ken-Ichi Takao, Kin-Ichi Tadano J Am Chem Soc. 2004 Sep 15;126(36):11254-67. doi: 10.1021/ja048320w.
A total synthesis of the macquarimicins A-C (1-3), novel natural products with intriguing tetra- or pentacyclic frameworks, has been achieved. The synthesis features an extensive investigation of the biosynthesis-based intramolecular Diels-Alder (IMDA) reactions of (E,Z,E)-1,6,8-nonatrienes. Considering possible biosynthetic sequences, four types of substrates were synthesized, and their IMDA reactions were examined. From one of the four substrates, the total synthesis was achieved via a transannular Diels-Alder reaction, which led to the stereoselective construction of the unique molecular framework. The convergent and efficient synthetic pathway afforded (+)-1 in 27 linear steps with 4.3% and 9.9% overall yields from readily available ethyl (2E,4S)-4,5-(isopropylidene)dioxy-2-pentenoate (22) and (R)-epichlorohydrin (30), respectively. Furthermore, efficient syntheses of 2, 3, and the 9-epi-cochleamycins A (57) and B (58) were accomplished. Additionally, the present work established the absolute stereochemistry of macquarimicins and revised the C(2)--C(3) geometry of 1.
2. Macquarimicins, microbial metabolites from Micromonospora. II. Isolation and structural elucidation
J E Hochlowski, M M Mullally, R Henry, D M Whittern, J B McAlpine J Antibiot (Tokyo). 1995 Jun;48(6):467-70. doi: 10.7164/antibiotics.48.467.
A novel series of carbocyclic compounds has been isolated from two related Micromonospora cultures. The C-19 and C-22 macquarimicins represent different end products on a similar biosynthetic scheme. 1-D and 2-D homonuclear and heteronuclear NMR experiments allowed assignment of the basic structures of the macquarimicins. An X-ray structure of macquarimicin B suggested the stereochemistry for the series which was not discernible from spectroscopic data alone.
3. Synthetic study of macquarimicins: highly stereoselective construction of the AB-ring system
R Munakata, T Ueki, H Katakai, K I Takao, K I Tadano Org Lett. 2001 Sep 20;3(19):3029-32. doi: 10.1021/ol016449u.
The highly stereoselective synthesis of the AB-ring system of macquarimicins, a novel class of microbial metabolites with inhibitory activity for neutral sphingomyelinase, has been achieved. The present synthesis features the highly stereocontrolled construction of the cis-tetrahydroindan structure via the intramolecular Diels-Alder reaction of an (E,Z,E)-1,6,8-nonatriene derived from D-glyceraldehyde acetonide. Reaction: see text.
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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 ╳
