Midecamycin A2
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| Category | Bioactive by-products |
| Catalog number | BBF-01936 |
| CAS | |
| Molecular Weight | 827.99 |
| Molecular Formula | C42H69NO15 |
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Description
Midecamycin A2 is a macrolide compound produced by Streptomyces mycarofaciens. It has strong anti-Gram-positive bacteria and weak anti-Gram-negative bacteria, mycobacteria and fungi activity. Cross-resistance with erythromycin.
Specification
| Synonyms | Antibiotic SF 837A2 |
| IUPAC Name | [(2S,3S,4R,6S)-6-[(2R,3S,4R,5R,6S)-4-(dimethylamino)-5-hydroxy-6-[[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-10-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-4-propanoyloxy-1-oxacyclohexadeca-11,13-dien-6-yl]oxy]-2-methyloxan-3-yl]oxy-4-hydroxy-2,4-dimethyloxan-3-yl] butanoate |
| Canonical SMILES | CCCC(=O)OC1C(OC(CC1(C)O)OC2C(OC(C(C2N(C)C)O)OC3C(CC(C(C=CC=CCC(OC(=O)CC(C3OC)OC(=O)CC)C)O)C)CC=O)C)C |
| InChI | InChI=1S/C42H69NO15/c1-11-16-32(47)56-40-27(6)53-34(23-42(40,7)50)57-37-26(5)54-41(36(49)35(37)43(8)9)58-38-28(19-20-44)21-24(3)29(45)18-15-13-14-17-25(4)52-33(48)22-30(39(38)51-10)55-31(46)12-2/h13-15,18,20,24-30,34-41,45,49-50H,11-12,16-17,19,21-23H2,1-10H3/b14-13+,18-15+/t24-,25-,26-,27+,28+,29+,30-,34+,35-,36-,37-,38+,39+,40+,41+,42-/m1/s1 |
| InChI Key | TYYIFWXTQAQRHI-MDWYKHENSA-N |
Properties
| Appearance | White Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; fungi; mycobacteria |
| Boiling Point | 881.1±65.0°C at 760 mmHg |
| Melting Point | 125-128°C |
| Density | 1.2±0.1 g/cm3 |
Reference Reading
1. Subcloning and expression of midecamycin polyketide synthase genes from Streptomyces mycarofaciens 1748
X Zhu, Y Wang, L Jin, X Xu Chin J Biotechnol. 1991;7(4):241-51.
A 2.4 kb fragment containing the midecamycin polyketide synthase genes (mps) was subcloned from the preliminary clone pCN8B12 out of the genomic library of midecamycin-producing strain S. mycarofaciens 1748, by using the homologous DNA of the actinorhodin polyketide synthase gene (act I) as hybridization probe. This DNA fragment was subcloned onto Streptomyces/E. coli shuttle vector pMHM3. A recombinant plasmid pCG2 was obtained. The transformation of the polyketide synthase deficient mutant of actinorhodin-producing strain, S. colicolor TK17, with pCG2 DNA resulted in the production of an antibacterial compound which was similar neither to actinorhodin nor to midecamycin. The transformation of spiramycin-producing strain S. ambofaciens with pCG2 DNA increased spiramycin production in the fermentation broth. The transformation of the regulatory mutant of daunorubicin-producing strain with pCG2 DNA resulted in the production of epsilon-rhodomycinone verified by TLC and HPLC analyses. The pCG2 DNA also could be functionally expressed in tetracenomycin C-producing strain S. glaucescens. However, it could not be expressed in the blocked mutants of erythromycin-producing strain Saccharopolyspora erythrarea WMH 15,261. These suggest that the pCG2 DNA may complement polyketide synthase gene deficiency or have some regulatory function in certain polyketide antibiotic-producing strains.
2. Characterization of polyketide ketoreductase gene (MPKR) from midecamycin-producing strain (Streptomyces mycarofaciens 1748)
H Xia, Y Wang, J Sun Chin J Biotechnol. 1994;10(3):169-78.
This paper presents the results about the expression of the polyketide ketoreductase gene from midecamycin-producing strain (S. mycarofaciens 1748), gene localization and nucleotide sequences analysis. A BamHI-BamHI 4.0 kg fragment isolated from a genomic library of midecamycin-producing strains containing the actIII homologous DNA was inserted into E. coli-Streptomyces shuttle vector pWHM3. A recombinant plasmid pCB4 was obtained and introduced into a 2-hydroxyaklavinone producer S. galilaeus ATCC 31671 that was a polyketide ketoreductase gene deficient mutant. The transformant produced aklavinone according to TLC and HPLC analyses. The BamHI-BamHI 4.0-kb fragment was inserted into pWHM3 in the reverted orientation with pCB4 and a recombinant plasmid pCBR4 was obtained. Introduction pCBR4 into S. galilaeus ATCC 31671 also resulted in the production of aklavinone. Thus we demonstrated that this gene encoded a polyketide ketoreductase which results in deoxygenation of 2-hydroxyaklavinone in C-2 position and that this gene has its own promoter. Restriction map analysis of pCB4 indicated that there were no sites for EcoRI and HindIII, but there were sites for BssHII, SalI, SphI and XhoI on the cloned gene fragment. The polyketide ketoreductase gene was located on a BssHII-BamHI 1.3-kb fragment from Southern hybridization result, using actIII gene as a probe, and that was confirmed by gene expression in S. galilaeus ATCC 31671. The nucleotide sequence analysis showed that the BssHII-BamHI 1.3-kb fragment contained an open reading frame (ORF). The protein coding region was assumed to start with an ATG start codon, end at an TAG stop codon. There was a 5nt (GGAGG) SD sequence at the upstream of start codon. A presumptive promoter consisted of 7 nt AACCGGA at the -10 region and 5 nt TTCGA at the -35 region. The deduced amino acid sequences of MPKR gene consisted of 261 aa residues. Its amino acid were compared with actIII gene coding protein sequences. The similarity was 77.4% and the identity was 66.7%.
3. [Studies on midecamycin 4"-O-propionyltransferase gene structure]
X Zhang, Y Wang Wei Sheng Wu Xue Bao. 1996 Dec;36(6):417-22.
A BamHI-BamHI 8.0 kb DNA fragment which contains midecamycin propionyltransferase (mpt) gene was digested with different restriction enzymes and the restriction map was made. The mpt gene was localized in a EcoRI-EcoRI-PstI3.0 kb DNA fragment by Southern blot analysis using a 2.4 kb DNA fragment of the CarE gene as a probe. The 3.0 kb DNA fragment of mpt gene was cloned into E. coli/Streptomyces shuttle vector pWHM3 and a recombinant plasmid pWFPE was obtained. S. ambofaciens(pWFPE) and S. lividans(pWFPE) can convert endogenously synthesized or exogenously added spiramycin into 4"-O-propionylspiramycin, respectively. Sequence analysis of mpt gene demonstrated an open reading frame in the EcoRI-EcoRI-PstI3.0 kb DNA fragment, which starts with ATG and ends with TGA. Mpt gene encodes a product of 388 aa. G+C mol% of mpt is 68.0 and G+C mol% of 3rd codon position is 91.5. The putative product of mpt has a identity of 67.6% and a similarity of 86.4% with CarE product. A consensus RBS GAGGT in the 6bp upstream from ATG and a promoter region were found. An inverted repeat sequence in the downstream from TGA acts as transcriptional terminator.
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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 ╳
