Amicoumacin C

Amicoumacin C

* Please be kindly noted products are not for therapeutic use. We do not sell to patients.

Category Antibiotics
Catalog number BBF-00438
CAS 77682-31-6
Molecular Weight 406.43
Molecular Formula C20H26N2O7

Online Inquiry

Description

It is produced by the strain of Bacillus pumilus BN-103. It is an antibiotic that resists gram-positive bacteria.

Specification

Synonyms D-ribo-Hexar-6-amic acid, 3-amino-2,3-dideoxy-N-[1-(3,4-dihydro-8-hydroxy-1-oxo-1H-2-benzopyran-3-yl)-3-methylbutyl]-, γ-lactone, [S-(R*,R*)]-; AI 77Ba; D-​ribo-​Hexonic acid, 3-​amino-​2,​3,​6-​trideoxy-​6-​[[(1S)​-​1-​[(3S)​-​3,​4-​dihydro-​8-​hydroxy-​1-​oxo-​1H-​2-​benzopyran-​3-​yl]​-​3-​methylbutyl]​amino]​-​6-​oxo-​, γ-​lactone
IUPAC Name (2S)-2-[(2S,3S)-3-Amino-5-oxooxolan-2-yl]-2-hydroxy-N-[(1S)-1-[(3S)-8-hydroxy-1-oxo-3,4-dihydroisochromen-3-yl]-3-methylbutyl]acetamide
Canonical SMILES CC(C)CC(C1CC2=C(C(=CC=C2)O)C(=O)O1)NC(=O)C(C3C(CC(=O)O3)N)O
InChI InChI=1S/C20H26N2O7/c1-9(2)6-12(22-19(26)17(25)18-11(21)8-15(24)29-18)14-7-10-4-3-5-13(23)16(10)20(27)28-14/h3-5,9,11-12,14,17-18,23,25H,6-8,21H2,1-2H3,(H,22,26)/t11-,12-,14-,17-,18-/m0/s1
InChI Key HVZSDRPOEPOHHS-YKRRISCLSA-N

Properties

Appearance Colorless Crystal
Antibiotic Activity Spectrum Gram-positive bacteria
Boiling Point 768.3±60.0 °C
Melting Point 131-133 °C
Density 1.345±0.06 g/cm3
Solubility Soluble in Methanol

Reference Reading

1. Asymmetric Total Synthesis of Hetiamacins A-F
Gang Wu, Ting Wang, Zhongke Jiang, Shaowei Liu, Chenghang Sun ACS Omega. 2021 Mar 17;6(12):8239-8245. doi: 10.1021/acsomega.0c06267. eCollection 2021 Mar 30.
Herein, we report a concise and stereoselective approach for the asymmetric total synthesis of hetiamacins A-F on the basis of the total synthesis of amicoumacin C, which could be synthesized from a known l-aspartic acid derivative. The synthesis of hetiamacin A was accomplished by an 11-step sequence that featured 1,3-oxazinane ring formation of amicoumacin B followed by amidation in one pot. Hetiamacins B-F were synthesized from amicoumacin A in only one step.
2. Application of Pd-Catalyzed C-H Alkylation Reaction in Total Syntheses of Twelve Amicoumacin-Type Natural Products
Hui-Hong Wang, Zhao Li, Yi-Yue Feng, Gao-Feng Yin, Tao Shi, Dian He, Xiao-Dong Wang, Zhen Wang Org Lett. 2021 Sep 3;23(17):6956-6960. doi: 10.1021/acs.orglett.1c02576. Epub 2021 Aug 23.
Enantioselective total syntheses of 12 amicoumacin-type natural products are accomplished with a palladium(II)-catalyzed C-H alkylation as the key step to furnish the 3,4-dihydroisocoumarin scaffold. The target chemicals are assembled in a convergent protocol by merging 3,4-dihydroisocoumarin derived amine part with categories of acid segments that are efficiently prepared by chemoselective catalytic oxidation of chiral 1,2-dihydroxyethylfuran-2(5H)-ones. Afterward, the cytotoxicity of amicoumacins on five cancer cell lines and one normal cell line is investigated.
3. Novel amylomacins from seaweed-associated Bacillus amyloliquefaciens as prospective antimicrobial leads attenuating resistant bacteria
Kajal Chakraborty, Vinaya Kizhakkepatt Kizhakkekalam, Minju Joy, Rekha Devi Chakraborty World J Microbiol Biotechnol. 2021 Oct 19;37(12):200. doi: 10.1007/s11274-021-03161-9.
The rise in antibiotic-resistant bacterial strains prompting nosocomial infections drives the search for new bioactive substances of promising antibacterial properties. The surfaces of seaweeds are rich in heterotrophic bacteria with prospective antimicrobial substances. This study aimed to isolate antibacterial leads from a seaweed-associated bacterium. Heterotrophic Bacillus amyloliquefaciens MTCC 12716 associated with the seaweed Hypnea valentiae, was isolated and screened for antimicrobial properties against drug-resistant pathogens. The bacterial crude extract was purified and three novel amicoumacin-class of isocoumarin analogues, 11'-butyl acetate amicoumacin C (amylomacin A), 4'-hydroxy-11'-methoxyethyl carboxylate amicoumacin C (amylomacin B) and 11'-butyl amicoumacin C (amylomacin C) were isolated to homogeneity. The studied amylomacins possessed potential activities against Pseudomonas aeruginosa, vancomycin-resistant Enterococcus faecalis, Klebsiella pneumoniae, methicillin-resistant Staphylococcus aureus, and Shigella flexneri with a range of minimum inhibitory concentration values from 0.78 to 3.12 µg/mL, although standard antibiotics ampicillin and chloramphenicol were active at 6.25-25 µg/mL. Noticeably, the amylomacin compound encompassing 4'-hydroxy-11'-methoxyethyl carboxylate amicoumacin C functionality (amylomacin B), displayed considerably greater antagonistic activities against methicillin-resistant S. aureus, vancomycin-resistant E. faecalis, Vibrio parahaemolyticus, Escherichia coli, and K. pneumoniae (minimum inhibitory concentration 0.78 μg/mL) compared to the positive controls and other amylomacin analogues. Antimicrobial properties of the amylomacins, coupled with the presence of polyketide synthase-I/non-ribosomal peptide synthetase hybrid gene attributed the bacterium as a promising source of antimicrobial compounds with pharmaceutical and biotechnological applications.

Bio Calculators

Stock concentration: *
Desired final volume: *
Desired concentration: *

L

* 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
g/mol
g

Recently viewed products

Online Inquiry

Verification code
cartIcon
Inquiry Basket