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XR586 Sale

目录号 : GC60387

XR586是一种肽类抗生素,从Acremoniumpersicinum发酵中分离得到。XR586含有几个α-氨基异丁酸(Aib)残基,缺少一个末端苯基丙醇,并在Phe-Gly序列终止。

XR586 Chemical Structure

Cas No.:185981-24-2

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5mg
¥7,875.00
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10mg
¥12,600.00
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产品描述

XR586 is a peptaibol-like antibiotic isolated from fermentations of Acremonium persicinum. XR586 contains several alpha-aminoisobutyric acid (Aib) residues, lacks a terminal phenylalaninol and terminates in the sequence Phe-Gly[1].

The mechanism of the anti-bacterial activity and toxicity: XR586 shows many structural and conformational features in common with peptaibols, particularly the zervamicins. Peptaibol antibiotics are peptides, typically of 15-20 residues, containing a large proportion of alpha-aminoisobutyric acid (Aib) residues. These peptides adopt a helical conformation in solution and display anti-bacterial and toxic properties due to their ability to form pores in membranes[1].

[1]. G J Sharman, et al. Structural elucidation of XR586, a peptaibol-like antibiotic from Acremonium persicinum. Biochem J. 1996 Dec 15; 320(Pt 3): 723-728.

Chemical Properties

Cas No. 185981-24-2 SDF
分子式 C91H138N20O22 分子量 1864.19
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1 mM 0.5364 mL 2.6821 mL 5.3643 mL
5 mM 0.1073 mL 0.5364 mL 1.0729 mL
10 mM 0.0536 mL 0.2682 mL 0.5364 mL
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Research Update

Structural elucidation of XR586, a peptaibol-like antibiotic from Acremonium persicinum

Biochem J 1996 Dec 15;320 ( Pt 3)(Pt 3):723-8.PMID:9003355DOI:10.1042/bj3200723.

A novel peptide, XR586, has been isolated from fermentations of Acremonium persicinum (Xenova culture collection number X21488). The structure of XR586 has been elucidated by means of NMR spectroscopy, electrospray and fast-atom bombardment MS, derivatization and enzymic digestion. It has been shown to be helical by CD measurements. XR586 shows many structural and conformational features in common with peptaibols, particularly the zervamicins. Peptaibol antibiotics are peptides, typically of 15-20 residues, containing a large proportion of alpha-aminoisobutyric acid (Aib) residues. These peptides adopt a helical conformation in solution and display anti-bacterial and toxic properties due to their ability to form pores in membranes. However, while XR586 contains several Aib residues, it lacks a terminal phenylalaninol and terminates in the sequence Phe-Gly. The lack of reduction of the penultimate residue at the C-terminus may indicate that this step is normally at the end of the biosynthetic pathway of peptaibols and occurs with cleavage of Gly. The 1H chemical shift assignments of XR586 are reported in Supplementary Publication SUP 50179 (3 pages), which has been deposited at the British Library Document Supply Centre, Boston Spa, Wetherby, West Yorkshire LS23 7BQ, U.K., from whom copies can be obtained on the terms indicated in Biochem. J. (1996) 313, 9 ("Deposition of data').

Acremotins A-D, peptaibiotics produced by the soil-derived fungus Acremonium persicinum SC0105

J Antibiot (Tokyo) 2018 Nov;71(11):927-938.PMID:30089870DOI:10.1038/s41429-018-0086-3.

Four new peptaibiotics, acremotins A-D (1-4) featuring three α,α-dialkylated amino acid-imino acid motifs and an unreduced C-terminal residue, along with the known peptaibiotic XR586 (5) were isolated from the solid cultures of the soil-derived fungus Acremonium persicinum SC0105. Their primary structures were characterized by detailed analysis of the HRESIMS/MS fragmentation pattern combined with comprehensive interpretation of the 1D and 2D NMR spectroscopic data. The absolute configurations of amino acid residues were determined by the advanced Marfey's method. Sequence alignment result shows that 1-4 are closely related to zervamicin IIB and emerimicin IIA, thus belong to peptaibiotic subfamily-3 (SF3). The three-dimensional (3D) structure of 4 was established by theoretical conformational analysis using the ab initio density functional theory (DFT) method, which, together with the CD spectrum, indicated an amphiphilic and helical structure for 4. 1-5 actively inhibited the growth of gram-positive bacterial pathogens, and amongst them 4 was the most potent compound showing MIC of 12.5 and 6.25 µg/ml against S. aureu and MRSA strains, respectively. 1-5 were also cytotoxic against three human cancer cell lines with IC50 ranging from 1.2 to 21.6 μM.