Lactonamycin Z
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| Category | Antibiotics |
| Catalog number | BBF-02229 |
| CAS | |
| Molecular Weight | 585.51 |
| Molecular Formula | C28H27NO13 |
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Description
It is produced by the strain of Streptomyces sp. AK 623. It's an antitumor antibiotic. It has weak anti-gram-positive bacterial activity. It can inhibit human tumor cells HMO2, MCF7 and Hep G2 with GI50 (μg/mL) of 1.9, 0.85 and 5.11, respectively.
Specification
| IUPAC Name | (15S,18S,22R)-15-[(2S,4R,5R,6S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-2,9-dihydroxy-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(C(CC(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)O |
| InChI | InChI=1S/C28H27NO13/c1-10-21(33)15(31)6-17(40-10)42-26-9-39-27(38-3)7-16(32)41-28(26,27)24(36)20-12(23(26)35)4-11-5-14(30)19-13(18(11)22(20)34)8-29(2)25(19)37/h4-5,10,15,17,21,30-31,33-34H,6-9H2,1-3H3/t10-,15+,17-,21-,26+,27-,28-/m0/s1 |
| InChI Key | FUPCTCUEYKCRGQ-LFIPHSLKSA-N |
Properties
| Appearance | Yellow Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Neoplastics (Tumor) |
| Solubility | Soluble in Methanol |
Reference Reading
1. 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.
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.
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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 ╳
