Lydimycin
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| Category | Antibiotics |
| Catalog number | BBF-02284 |
| CAS | 10118-85-1 |
| Molecular Weight | 242.30 |
| Molecular Formula | C10H14N2O3S |
| Purity | 95% |
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Description
It is produced by the strain of Str. lydicus NRRL 2433. It has a broad spectrum of anti-bacterial and mycobacterial effects. Biotin can counteract its antibacterial activity in the synthetic medium.
Specification
| Synonyms | Lidimycin; alpha-Dehydrobiotin; Lidimicina; Lidimycine; 2-Pentenoic acid, 5-(hexahydro-2-oxo-1H-thieno(3,4-d)imidazol-4-yl)-, (3aS(3aalpha,4beta,6aalpha))-; (+)-α-trans-Dehydrobiotin; [E,(+)]-5-[(3aS,4S,6aR)-Hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-4α-yl]-2-pentenoic acid; (E)-2,3-didehydro-biotin |
| IUPAC Name | (E)-5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pent-2-enoic acid |
| Canonical SMILES | C1C2C(C(S1)CCC=CC(=O)O)NC(=O)N2 |
| InChI | InChI=1S/C10H14N2O3S/c13-8(14)4-2-1-3-7-9-6(5-16-7)11-10(15)12-9/h2,4,6-7,9H,1,3,5H2,(H,13,14)(H2,11,12,15)/b4-2+/t6-,7-,9-/m0/s1 |
| InChI Key | NZERRTYPTPRCIR-ARSLAPBQSA-N |
Properties
| Appearance | White Crystal |
| Antibiotic Activity Spectrum | Mycobacteria |
| Boiling Point | 593.0°C at 760 mmHg |
| Melting Point | 238-240°C |
| Density | 1.30 g/cm3 |
| Solubility | Soluble in Water, Sodium hydroxide |
Reference Reading
1. Streptomyces lydicamycinicus sp. nov. and Its Secondary Metabolite Biosynthetic Gene Clusters for Polyketide and Nonribosomal Peptide Compounds
Hisayuki Komaki, Akira Hosoyama, Yasuhiro Igarashi, Tomohiko Tamura Microorganisms. 2020 Mar 6;8(3):370. doi: 10.3390/microorganisms8030370.
(1) Background: Streptomyces sp. TP-A0598 derived from seawater produces lydicamycin and its congeners. We aimed to investigate its taxonomic status; (2) Methods: A polyphasic approach and whole genome analysis are employed; (3) Results: Strain TP-A0598 contained ll-diaminopimelic acid, glutamic acid, glycine, and alanine in its peptidoglycan. The predominant menaquinones were MK-9(H6) and MK-9(H8), and the major fatty acids were C16:0, iso-C15:0, iso-C16:0, and anteiso-C15:0. Streptomyces sp. TP-A0598 showed a 16S rDNA sequence similarity value of 99.93% (1 nucleottide difference) to Streptomyces angustmyceticus NRRL B-2347T. The digital DNA-DNA hybridisation value between Streptomyces sp. TP-A0598 and its closely related type strains was 25%-46%. Differences in phenotypic characteristics between Streptomyces sp. TP-A0598 and its phylogenetically closest relative, S. angustmyceticus NBRC 3934T, suggested strain TP-A0598 to be a novel species. Streptomyces sp. TP-A0598 and S. angustmyceticus NBRC 3934T harboured nine and 13 biosynthetic gene clusters for polyketides and nonribosomal peptides, respectively, among which only five clusters were shared between them, whereas the others are specific for each strain; and (4) Conclusions: For strain TP-A0598, the name Streptomyces lydicamycinicus sp. nov. is proposed; the type strain is TP-A0598T (=NBRC 110027T).
2. Draft genome sequence of marine-derived Streptomyces sp. TP-A0598, a producer of anti-MRSA antibiotic lydicamycins
Hisayuki Komaki, Natsuko Ichikawa, Akira Hosoyama, Nobuyuki Fujita, Yasuhiro Igarashi Stand Genomic Sci. 2015 Aug 26;10:58. doi: 10.1186/s40793-015-0046-5. eCollection 2015.
Streptomyces sp. TP-A0598, isolated from seawater, produces lydicamycin, structurally unique type I polyketide bearing two nitrogen-containing five-membered rings, and four congeners TPU-0037-A, -B, -C, and -D. We herein report the 8 Mb draft genome sequence of this strain, together with classification and features of the organism and generation, annotation and analysis of the genome sequence. The genome encodes 7,240 putative ORFs, of which 4,450 ORFs were assigned with COG categories. Also, 66 tRNA genes and one rRNA operon were identified. The genome contains eight gene clusters involved in the production of polyketides and nonribosomal peptides. Among them, a PKS/NRPS gene cluster was assigned to be responsible for lydicamycin biosynthesis and a plausible biosynthetic pathway was proposed on the basis of gene function prediction. This genome sequence data will facilitate to probe the potential of secondary metabolism in marine-derived Streptomyces.
3. Alchivemycin A, a bioactive polycyclic polyketide with an unprecedented skeleton from Streptomyces sp
Yasuhiro Igarashi, Youngju Kim, Yasuko In, Toshimasa Ishida, Yukiko Kan, Tsuyoshi Fujita, Takashi Iwashita, Hirokazu Tabata, Hiroyasu Onaka, Tamotsu Furumai Org Lett. 2010 Aug 6;12(15):3402-5. doi: 10.1021/ol1012982.
Alchivemycin A, a novel polycyclic polyketide, was isolated from the culture extract of a plant-derived actinomycete Streptomyces sp. The structure and relative configuration were elucidated by spectroscopic analysis and X-ray crystallography, and the absolute configuration was determined by a (1)H NMR anisotropy method using MPA ester derivatization. The new compound contains an unprecedented heterocyclic ring system, 2H-tetrahydro-4,6-dioxo-1,2-oxazine. Alchivemycin A showed potent antimicrobial activity against Micrococcus luteus and inhibitory effects on tumor cell invasion.
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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 ╳
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