Arylomycin A2
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| Category | Antibiotics |
| Catalog number | BBF-00095 |
| CAS | |
| Molecular Weight | 824.97 |
| Molecular Formula | C42H60N6O11 |
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Description
Arylomycin A is a lipopeptide compound with double aryl bridge produced by Streptomyces sp. Tu 6076. It has anti-Gram-positive bacteria activity. The most sensitive bacteria is Rhodococcus Ehmpolis.
Specification
| IUPAC Name | (8R,11R,14R)-3,18-dihydroxy-14-[[2-[[(2S)-2-[[(2S)-3-hydroxy-2-[methyl(10-methylundecanoyl)amino]propanoyl]amino]propanoyl]amino]acetyl]-methylamino]-11-methyl-10,13-dioxo-9,12-diazatricyclo[13.3.1.12,6]icosa-1(18),2,4,6(20),15(19),16-hexaene-8-carboxylic acid |
| Canonical SMILES | CC1C(=O)NC(CC2=CC(=C(C=C2)O)C3=C(C=CC(=C3)C(C(=O)N1)N(C)C(=O)CNC(=O)C(C)NC(=O)C(CO)N(C)C(=O)CCCCCCCCC(C)C)O)C(=O)O |
| InChI | InChI=1S/C42H60N6O11/c1-24(2)13-11-9-7-8-10-12-14-35(52)47(5)32(23-49)40(56)44-25(3)38(54)43-22-36(53)48(6)37-28-16-18-34(51)30(21-28)29-19-27(15-17-33(29)50)20-31(42(58)59)46-39(55)26(4)45-41(37)57/h15-19,21,24-26,31-32,37,49-51H,7-14,20,22-23H2,1-6H3,(H,43,54)(H,44,56)(H,45,57)(H,46,55)(H,58,59)/t25-,26+,31+,32-,37+/m0/s1 |
| InChI Key | YFSXYWAZCKMYJN-YSEAOSKOSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria |
Reference Reading
1. Macrolactamization Approaches to Arylomycin Antibiotics Core
Ngiap-Kie Lim, Xin Linghu, Nicholas Wong, Haiming Zhang, C Gregory Sowell, Francis Gosselin Org Lett. 2019 Jan 4;21(1):147-151. doi: 10.1021/acs.orglett.8b03603. Epub 2018 Dec 19.
Two practical entries to arylomycin antibiotics core structures are investigated. In route A, the activation of l-Hpg for the key macrolactamization step is achieved in 89% yield in the presence of unprotected phenol and amine functionalities. Alternatively, a propanephosphonic acid anhydride (T3P)-promoted coupling between thel-Tyr and l-Ala moieties in route B led to a facile macrolactamization in 68% yield with a marked reduction in competing oligomerization.
2. Carrier Protein-Free Enzymatic Biaryl Coupling in Arylomycin A2 Assembly and Structure of the Cytochrome P450 AryC
Hülya Aldemir, Shuangjie Shu, Francoise Schaefers, Hanna Hong, René Richarz, Sabrina Harteis, Manuel Einsiedler, Tobias M Milzarek, Sabine Schneider, Tobias A M Gulder Chemistry. 2022 Jan 10;28(2):e202104451. doi: 10.1002/chem.202104451. Epub 2021 Dec 27.
Invited for the cover of this issue are Sabine Schneider, Tobias A. M. Gulder and co-workers at Technical University of Dresden, Technical University of Munich and Ludwig-Maximillians-University Munich. The image depicts the crystal structure of the cytochrome P450 AryC from arylomycin biosynthesis. Read the full text of the article at 10.1002/chem.202103389.
3. Carrier Protein-Free Enzymatic Biaryl Coupling in Arylomycin A2 Assembly and Structure of the Cytochrome P450 AryC
Hülya Aldemir, Shuangjie Shu, Francoise Schaefers, Hanna Hong, René Richarz, Sabrina Harteis, Manuel Einsiedler, Tobias M Milzarek, Sabine Schneider, Tobias A M Gulder Chemistry. 2022 Jan 10;28(2):e202103389. doi: 10.1002/chem.202103389. Epub 2021 Nov 26.
The arylomycin antibiotics are potent inhibitors of bacterial type I signal peptidase. These lipohexapeptides contain a biaryl structural motif reminiscent of glycopeptide antibiotics. We herein describe the functional and structural evaluation of AryC, the cytochrome P450 performing biaryl coupling in biosynthetic arylomycin assembly. Unlike its enzymatic counterparts in glycopeptide biosynthesis, AryC converts free substrates without the requirement of any protein interaction partner, likely enabled by a strongly hydrophobic cavity at the surface of AryC pointing to the substrate tunnel. This activity enables chemo-enzymatic assembly of arylomycin A2 that combines the advantages of liquid- and solid-phase peptide synthesis with late-stage enzymatic cross-coupling. The reactivity of AryC is unprecedented in cytochrome P450-mediated biaryl construction in non-ribosomal peptides, in which peptidyl carrier protein (PCP)-tethering so far was shown crucial both in vivo and in vitro.
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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 ╳
