Unusual Acetylation-Elimination in the Formation of Tetronate Antibiotics
Unusual Acetylation-Elimination in the Formation of Tetronate Antibiotics
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DOI：
10.1002/anie.201301680
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发表时间：
2013-01-01
影响因子：
16.6
通讯作者：
Leadlay, Peter F.
中科院分区：
文献类型：
--
作者：
Kanchanabanca, Chompoonik;Tao, Weixin;Leadlay, Peter F.
四酸盐抗生素是一类重要且不断发展的聚酮类天然产物，具有四酸盐（4-羟基-[5H]呋喃-2- 1）环体系的特征。它们已从陆地和海洋细菌中分离出来，并表现出多种生物活性它们包括四酸酯聚醚tetronate poly醚tetronomycin[2]和tetronasin，[3]脂肪酰基四酸酯抗生素凝集蛋白[4]和结构密切相关的蛋白磷酸酶抑制剂RK-682[5]（图1）。特别令人感兴趣的是结构有趣的螺戊酸酯（图1a），包括抗菌化合物氯霉素[6]和阿比索菌素[7]，抗病毒化合物四氯霉素[8]和抗肿瘤化合物河蟹素[9]和kijanimicin [10]这些化合物似乎是在初始形成的四酸盐前体经过特定脱水后，通过酶催化的Diels-Alder反应[11]产生的，如图1b中atrop-abyssomicin C[7]所示。
Tetronate antibiotics comprise an important and growing family of polyketide natural products possessing a characteristic tetronate (4-hydroxy-[5H] furan-2-one) ring system. They have been isolated from both terrestrial and marine bacteria, and show a diverse range of biological activities.[1] They include the tetronate polyethers tetronomycin [2] and tetronasin,[3] the fatty acyltetronate antibiotic agglomerin,[4] and the structurally closely related protein phosphatase inhibitor RK-682 [5](Figure 1). Of particular interest are the structurally intriguing spirotetronates (Figure 1a), including the antibacterial compounds chlorothricin [6] and abyssomicin,[7] the antiviral compound quartromicin,[8] and the antitumour compounds tetrocarcin [9] and kijanimicin.[10] These compounds appear to arise through an enzyme-catalyzed Diels–Alder reaction [11] after specific dehydration of an initially formed tetronate precursor, as shown for atrop-abyssomicin C [7] in Figure 1b.