Lactonamycin
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| Category | Antibiotics |
| Catalog number | BBF-02642 |
| CAS | 182234-02-2 |
| Molecular Weight | 569.51 |
| Molecular Formula | C28H27NO12 |
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Description
It is produced by the strain of Streptomyces rishiriensis MJ 773-88K4. It had strong activity against gram-positive bacteria including staphylococcus, streptococcus, enterococcus, MRSA (MIC is 0.39-0.78 μg/mL) and VRE (MIC is 0.39-0.78 μg/mL). It also has inhibitory effect on L-1210, P388, S180, FS-3, Ehrlich, B16-BL5 and other tumor cell lines (IC50 is 0.06-3.3 μg/mL).
Specification
| Synonyms | (3aS,5aS,14aR)-9,13-dihydroxy-5a-{[(2S,5S,6S)-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-3a-methoxy-11-methyl-3,3a,11,12-tetrahydro-2H,5H-furo[2'',3'':4',5']furo[3',4':6,7]naphtho[2,3-e]isoindole-2,6,10,14(5aH)-tetrone; (+)-Lactonamycin |
| IUPAC Name | (15S,18S,22R)-2,9-dihydroxy-15-[(2S,5S,6S)-5-hydroxy-6-methyloxan-2-yl]oxy-18-methoxy-6-methyl-17,21-dioxa-6-azahexacyclo[11.10.0.03,11.04,8.015,22.018,22]tricosa-1(13),2,4(8),9,11-pentaene-7,14,20,23-tetrone |
| Canonical SMILES | CC1C(CCC(O1)OC23COC4(C2(C(=O)C5=C(C3=O)C=C6C=C(C7=C(C6=C5O)CN(C7=O)C)O)OC(=O)C4)OC)O |
| InChI | InChI=1S/C28H27NO12/c1-11-15(30)4-5-18(39-11)41-26-10-38-27(37-3)8-17(32)40-28(26,27)24(35)21-13(23(26)34)6-12-7-16(31)20-14(19(12)22(21)33)9-29(2)25(20)36/h6-7,11,15,18,30-31,33H,4-5,8-10H2,1-3H3/t11-,15-,18-,26+,27-,28-/m0/s1 |
| InChI Key | XFQJOLWXLJXJSV-VUAGTGNDSA-N |
Properties
| Appearance | Pale Yellow Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Neoplastics (Tumor) |
| Boiling Point | 943.0°C at 760 mmHg |
| Melting Point | 168-171°C |
| Density | 1.67 g/cm3 |
| Solubility | Soluble in Methanol, Ethyl Acetate |
Reference Reading
1. Studies on the total synthesis of lactonamycin: construction of model ABCD ring systems
David A Henderson, Philip N Collier, Gregoire Pavé, Paula Rzepa, Andrew J P White, Jeremy N Burrows, Anthony G M Barrett J Org Chem. 2006 Mar 17;71(6):2434-44. doi: 10.1021/jo052637c.
Model studies on the synthesis of the tetracyclic ABCD ring system of lactonamycin (1) are described. The key step involved the double Michael addition reaction of alcohol 8 to propynoate esters to produce the BCD units 13 and 14 of the target 1. Alternatively, double Michael addition of alcohol 8 to di-tert-butyl acetylenedcarboxylate gave the corresponding BCD ring systems 36 and 37. Acid-mediated hydrolysis of the dihydroquinone monoketal units of 13 and 14 and 36 and 37 in the presence of air gave the corresponding quinones 7 and 39. These were converted into the tetracyclic ABCD units 6, 26a, 40, and 42 of lactonamycin (1) by either dihydroxylation or epoxidation and acid-catalyzed lactonization.
2. Biosynthetic investigations of lactonamycin and lactonamycin z: cloning of the biosynthetic gene clusters and discovery of an unusual starter unit
Xiujun Zhang, Lawrence B Alemany, Hans-Peter Fiedler, Michael Goodfellow, Ronald J Parry Antimicrob Agents Chemother. 2008 Feb;52(2):574-85. doi: 10.1128/AAC.00717-07. Epub 2007 Dec 10.
The antibiotics lactonamycin and lactonamycin Z provide attractive leads for antibacterial drug development. Both antibiotics contain a novel aglycone core called lactonamycinone. To gain insight into lactonamycinone biosynthesis, cloning and precursor incorporation experiments were undertaken. The lactonamycin gene cluster was initially cloned from Streptomyces rishiriensis. Sequencing of ca. 61 kb of S. rishiriensis DNA revealed the presence of 57 open reading frames. These included genes coding for the biosynthesis of l-rhodinose, the sugar found in lactonamycin, and genes similar to those in the tetracenomycin biosynthetic gene cluster. Since lactonamycin production by S. rishiriensis could not be sustained, additional proof for the identity of the S. rishiriensis cluster was obtained by cloning the lactonamycin Z gene cluster from Streptomyces sanglieri. Partial sequencing of the S. sanglieri cluster revealed 15 genes that exhibited a very high degree of similarity to genes within the lactonamycin cluster, as well as an identical organization. Double-crossover disruption of one gene in the S. sanglieri cluster abolished lactonamycin Z production, and production was restored by complementation. These results confirm the identity of the genetic locus cloned from S. sanglieri and indicate that the highly similar locus in S. rishiriensis encodes lactonamycin biosynthetic genes. Precursor incorporation experiments with S. sanglieri revealed that lactonamycinone is biosynthesized in an unusual manner whereby glycine or a glycine derivative serves as a starter unit that is extended by nine acetate units. Analysis of the gene clusters and of the precursor incorporation data suggested a hypothetical scheme for lactonamycinone biosynthesis.
3. An Approach to the Core of Lactonamycin
Philip J Parsons, Daniel R Jones, Lee J Walsh, Lewis A T Allen, Ada Onwubiko, Lewis Preece, Johnathan Board, Andrew J P White Org Lett. 2017 May 19;19(10):2533-2535. doi: 10.1021/acs.orglett.7b00902. Epub 2017 Apr 26.
A cascade reaction has been developed for the synthesis of lactonamycin. In this paper, we demonstrate that a transition-metal-free thermal ene-diyne cyclization can be used for the construction of the entire core of the antibiotic lactonamycin and anticancer agent lactonamycin Z.
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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 ╳
