Macquarimicin C
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| Category | Antibiotics |
| Catalog number | BBF-02288 |
| CAS | 165561-12-6 |
| Molecular Weight | 370.44 |
| Molecular Formula | C22H26O5 |
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Description
It is produced by the strain of Micromonospora chalcea. It's an antibiotic.
Specification
| Synonyms | 2H-8,10a-Ethanocyclopenta[7,8]naphtho[2,3-c]pyran-3,10,12-trione,1,3a,5a,6,6a,7,8,11,11a,11b-decahydro-2-methyl-11-(2-oxopropyl)-,(2R,3aS,5aS,6aS,8R,10aR,11S,11aS,11bR)-; 10H-8,10a-Ethanocyclopenta[7,8]naphtho[2,3-c]pyran-3,10,12(2H)-trione,1,3a,5a,6,6a,7,8,11,11a,11b-decahydro-2-methyl-11-(2-oxopropyl)-, (2R,3aS,5aS,6aS,8R,10aR,11S,11aS,11bR)- |
| IUPAC Name | (1R,2S,3S,4R,6R,8S,11S,13S,15R)-6-methyl-2-(2-oxopropyl)-16-oxapentacyclo[13.2.2.01,13.03,11.04,8]nonadec-9-ene-7,17,18-trione |
| Canonical SMILES | CC1CC2C(C1=O)C=CC3C2C(C45C(C3)CC(CC4=O)OC5=O)CC(=O)C |
| InChI | InChI=1S/C22H26O5/c1-10-5-16-15(20(10)25)4-3-12-7-13-8-14-9-18(24)22(13,21(26)27-14)17(19(12)16)6-11(2)23/h3-4,10,12-17,19H,5-9H2,1-2H3/t10-,12-,13+,14-,15+,16+,17+,19+,22-/m1/s1 |
| InChI Key | ZKSMHLMCOSXDEO-SZBVIKRBSA-N |
Reference Reading
1. 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.
2. 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.
3. 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.
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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 ╳
