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卡里曼他星/巴图霉素类抗生素的相对及绝对立体化学解析

Elucidation of the relative and absolute stereochemistry of the kalimantacin/batumin antibiotics.

作者信息

Thistlethwaite Iain R G, Bull Freya M, Cui Chengsen, Walker Paul D, Gao Shu-Shan, Wang Luoyi, Song Zhongshu, Masschelein Joleen, Lavigne Rob, Crump Matthew P, Race Paul R, Simpson Thomas J, Willis Christine L

机构信息

School of Chemistry , University of Bristol , Cantock's Close , Bristol BS8 1TS , UK . Email:

Laboratory of Gene Technology , KULeuven , Leuven B-3001 , Belgium.

出版信息

Chem Sci. 2017 Sep 1;8(9):6196-6201. doi: 10.1039/c7sc01670k. Epub 2017 Jul 11.

DOI:10.1039/c7sc01670k
PMID:28989652
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5628338/
Abstract

Kalimantacin A and batumin exhibit potent and selective antibiotic activity against species including MRSA. Both compounds are formed a hybrid polyketide synthase/non-ribosomal peptide synthetase (PKS-NRPS) biosynthetic pathway and from comparison of the gene clusters it is apparent that batumin from and kalimantacin from are the same compound. The linear structure of this unsaturated acid was assigned by spectroscopic methods, but the relative and absolute stereochemistry of the five stereocentres remained unknown. Herein we describe isolation of kalimantacin A and two further metabolites 17,19-diol and 27-descarbomyl hydroxyketone from cultures of . Their absolute and relative stereochemistries are rigorously determined using a multidisciplinary approach combining natural product degradation and fragment synthesis with bioinformatics and NMR spectroscopy. Diol has the 5, 15, 17, 19, 26, 27 configuration and is the immediate biosynthetic precursor of the bioactive kalimantacin A formed by oxidation of the 17-alcohol to the ketone.

摘要

卡里曼他星A和巴图明对包括耐甲氧西林金黄色葡萄球菌（MRSA）在内的多种菌种表现出强效且具选择性的抗生素活性。这两种化合物均由混合聚酮合酶/非核糖体肽合成酶（PKS-NRPS）生物合成途径形成，通过对基因簇的比较，很明显来自[具体来源1]的巴图明和来自[具体来源2]的卡里曼他星是同一化合物。这种不饱和酸的线性结构通过光谱方法确定，但五个立体中心的相对和绝对立体化学仍不清楚。在此，我们描述了从[具体菌种]培养物中分离出卡里曼他星A以及另外两种代谢产物17,19 -二醇和27 -去甲酰基羟基酮。我们采用多学科方法，将天然产物降解、片段合成与生物信息学和核磁共振光谱相结合，严格确定了它们的绝对和相对立体化学。二醇具有5, 15, 17, 19, 26, 27构型，是通过将17 -醇氧化为酮而形成的生物活性卡里曼他星A的直接生物合成前体。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7cfd/5628338/efb00d2208c5/c7sc01670k-s7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7cfd/5628338/c36ed16b0a0c/c7sc01670k-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7cfd/5628338/db9e31dda185/c7sc01670k-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7cfd/5628338/8e88d487cfca/c7sc01670k-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7cfd/5628338/7f8e5140953d/c7sc01670k-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7cfd/5628338/08b896c66a6c/c7sc01670k-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7cfd/5628338/20381f00bfab/c7sc01670k-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7cfd/5628338/7d2b9ff60af2/c7sc01670k-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7cfd/5628338/a0686a748a45/c7sc01670k-s6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7cfd/5628338/efb00d2208c5/c7sc01670k-s7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7cfd/5628338/c36ed16b0a0c/c7sc01670k-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7cfd/5628338/db9e31dda185/c7sc01670k-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7cfd/5628338/8e88d487cfca/c7sc01670k-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7cfd/5628338/7f8e5140953d/c7sc01670k-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7cfd/5628338/08b896c66a6c/c7sc01670k-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7cfd/5628338/20381f00bfab/c7sc01670k-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7cfd/5628338/7d2b9ff60af2/c7sc01670k-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7cfd/5628338/a0686a748a45/c7sc01670k-s6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7cfd/5628338/efb00d2208c5/c7sc01670k-s7.jpg

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