Lankamycin
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-02233 |
| CAS | 30042-37-6 |
| Molecular Weight | 833.02 |
| Molecular Formula | C42H72O16 |
| Purity | 98% |
Online Inquiry
Description
It is produced by the strain of Str. violaceoniger NRRL 2834. It's a macrolide antibiotic. It has weak anti-gram-positive bacterial activity. It has cross-resistance with Picromycin and synergistic effect with Lankacidin.
Specification
| Synonyms | Lankavamycin; Kujimycin B; Antibiotic A-20338-N2; [3R-[3R*,4S*,5R*,6S*,7S*,9S*,11R*,12S*,13S*,14R*(1S*,2S*)]]-4-[(4-O-Acetyl-2,6-dideoxy-3-C-methyl-3-O-methyl-a-L-xylo-hexopyranosyl)oxy]-12-(acetyloxy)-6-[(4,6-dideoxy-3-O-methyl-b-D-xylo-hexopyranosyl)oxy]-9-hydroxy-14-(2-hydroxy-1-methylpropyl)-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione |
| IUPAC Name | [(2R,3S,4S,5R,7S,9S,10S,11R,12S,13R)-12-[(2R,4R,5R,6S)-5-acetyloxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-7-hydroxy-2-[(2S,3S)-3-hydroxybutan-2-yl]-10-[(2S,3R,4S,6R)-3-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-6,14-dioxo-oxacyclotetradec-4-yl] acetate |
| Canonical SMILES | CC1CC(C(C(O1)OC2C(CC(C(=O)C(C(C(C(OC(=O)C(C(C2C)OC3CC(C(C(O3)C)OC(=O)C)(C)OC)C)C(C)C(C)O)C)OC(=O)C)C)(C)O)C)O)OC |
| InChI | InChI=1S/C42H72O16/c1-19-17-41(12,49)37(47)24(6)35(54-28(10)44)23(5)34(21(3)26(8)43)57-39(48)25(7)36(22(4)33(19)58-40-32(46)30(50-14)16-20(2)52-40)56-31-18-42(13,51-15)38(27(9)53-31)55-29(11)45/h19-27,30-36,38,40,43,46,49H,16-18H2,1-15H3/t19-,20+,21-,22+,23-,24+,25+,26-,27-,30-,31-,32+,33-,34+,35-,36-,38+,40-,41-,42+/m0/s1 |
| InChI Key | JQMACDQCTNFQMM-QAOHEUSVSA-N |
Properties
| Appearance | Colorless Amorphous Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 846.0±65.0°C (Predicted) |
| Melting Point | 146-147°C |
| Density | 1.19±0.1 g/cm3 (Predicted) |
| Solubility | Soluble in Ethanol |
Reference Reading
1. Accumulation of lankamycin derivative with a branched-chain sugar from a blocked mutant of chalcose biosynthesis in Streptomyces rochei 7434AN4
Mingge Zhang, Bao Shuang, Kenji Arakawa Bioorg Med Chem Lett. 2023 Jan 15;80:129125. doi: 10.1016/j.bmcl.2023.129125. Epub 2023 Jan 5.
Lankamycin, a macrolide antibiotic produced by Streptomyces rochei 7434AN4, exhibits a moderate antimicrobial activity and acts as a synergistic pair with carbocyclic antibiotic lankacidin C by binding to the ribosome exit tunnel. Its biosynthetic gene (lkm) cluster (orf24-orf53) is located on the largest plasmid pSLA2-L (210,614 bp). Our group possesses a variety of lankamycin derivatives and macrolide-modification enzymes including P450 enzymes and glycosyltransferases, which may lead to expand the chemical library of bioactive macrolides. Here we constructed a mutant of a 3-ketoreductase gene lkmCVI (orf42) involved in d-chalcose biosynthesis, and its metabolite was isolated and structure-elucidated. Accumulation of novel lankamycin derivative harboring a branched-chain deoxysugar, 5-O-(4',6'-dideoxy-3'-C-acetyl-d-ribo-hexopyranosyl)-3-O-(4″-O-acetyl-l-arcanosyl)-lankanolide, indicated that LkmCVI acts as a gate keeper enzyme for d-chalcose synthesis in lankamycin biosynthesis.
2. SrrB, a Pseudo-Receptor Protein, Acts as a Negative Regulator for Lankacidin and Lankamycin Production in Streptomyces rochei
Yuya Misaki, Shouji Yamamoto, Toshihiro Suzuki, Miyuki Iwakuni, Hiroaki Sasaki, Yuzuru Takahashi, Kuninobu Inada, Haruyasu Kinashi, Kenji Arakawa Front Microbiol. 2020 Jun 9;11:1089. doi: 10.3389/fmicb.2020.01089. eCollection 2020.
Streptomyces rochei 7434AN4, a producer of lankacidin (LC) and lankamycin (LM), carries many regulatory genes including a biosynthesis gene for signaling molecules SRBs (srrX), an SRB receptor gene (srrA), and a SARP (Streptomyces antibiotic regulatory protein) family activator gene (srrY). Our previous study revealed that the main regulatory cascade goes from srrX through srrA to srrY, leading to LC production, whereas srrY further regulates a second SARP gene srrZ to synthesize LM. In this study we extensively investigated the function of srrB, a pseudo-receptor gene, by analyzing antibiotic production and transcription. Metabolite analysis showed that the srrB mutation increased both LC and LM production over four-folds. Transcription, gel shift, and DNase I footprinting experiments revealed that srrB and srrY are expressed under the SRB/SrrA regulatory system, and at the later stage, SrrB represses srrY expression by binding to the promoter region of srrY. These findings confirmed that SrrB acts as a negative regulator of the activator gene srrY to control LC and LM production at the later stage of fermentation in S. rochei.
3. Substrate specificity of two cytochrome P450 monooxygenases involved in lankamycin biosynthesis
Aiko Teshima, Hisashi Kondo, Yu Tanaka, Yosi Nindita, Yuya Misaki, Yuji Konaka, Yasuhiro Itakura, Tsugumi Tonokawa, Haruyasu Kinashi, Kenji Arakawa Biosci Biotechnol Biochem. 2021 Jan 7;85(1):115-125. doi: 10.1093/bbb/zbaa063.
To elucidate the gross lankamycin biosynthetic pathway including two cytochrome P450 monooxygenases, LkmK and LkmF, we constructed two double mutants of P450 genes in combination with glycosyltransferase genes, lkmL and lkmI. An aglycon 8,15-dideoxylankanolide, a possible substrate for LkmK, was prepared from an lkmK-lkmL double mutant, while a monoglycoside 3-O-l-arcanosyl-8-deoxylankanolide, a substrate for LkmF, was from an lkmF-lkmI double mutant. Bioconversion of lankamycin derivatives was performed in the Escherichia coli recombinant for LkmK and the Streptomyces lividans recombinant for LkmF, respectively. LkmK catalyzes the C-15 hydroxylation on all 15-deoxy derivatives, including 8,15-dideoxylankanolide (a possible substrate), 8,15-dideoxylankamycin, and 15-deoxylankamycin, suggesting the relaxed substrate specificity of LkmK. On the other hand, LkmF hydroxylates the C-8 methine of 3-O-l-anosyl-8-deoxylankanolide. Other 8-deoxy lankamycin/lankanolide derivatives were not oxidized, suggesting the importance of a C-3 l-arcanosyl moiety for substrate recognition by LkmF in lankamycin biosynthesis. Thus, LkmF has a strict substrate specificity in lankamycin biosynthesis.
Recommended Products
| BBF-03755 | Actinomycin D | Inquiry |
| BBF-03754 | CASTANOSPERMINE | Inquiry |
| BBF-05862 | Epirubicin | Inquiry |
| BBF-01829 | Deoxynojirimycin | Inquiry |
| BBF-01693 | Doxorubicin EP Impurity A (Daunorubicin) | Inquiry |
| BBF-02642 | Lactonamycin | Inquiry |
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 ╳
