Tenuecyclamides A-D, cyclic hexapeptides from the cyanobacterium Nostoc spongiaeforme var. tenue

Tenuecyclamides A-D, cyclic hexapeptides from the cyanobacterium Nostoc spongiaeforme var. tenue
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DOI:
10.1021/np980138j
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发表时间:
1998-10-01
影响因子:
5.1
通讯作者:
Carmeli, S
Carmeli, S
中科院分区:
生物学2区
文献类型:
--
作者:
Banker, R;Carmeli, S

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从海绵状Nostoc spongiaeformme var, tenue菌株IL-184-6的甲醇提取物中分离出4个修饰的环六肽tenuecyclamides A-D(1-4)和已知的抗生素borophycin(5)。采用同核、反异核2D-NMR技术以及高分辨率质谱测定了tenuecyclamides A-D(1-4)的平面结构。采用Marfey高效液相色谱法研究了不对称中心的绝对构型。tenuecyclamides A和B的不对称中心(1和2)的立体化学不能完全确定,而tenuecyclamides C和D的不对称中心(3和4)的立体化学是明确的。
Four modified cyclic hexapeptides, tenuecyclamides A-D (1-4), were isolated along with the known antibiotic, borophycin (5), from the methanol extract of Nostoc spongiaeforme var, tenue (TAU strain IL-184-6). The planar structure of tenuecyclamides A-D (1-4) was determined by homonuclear and inverse-heteronuclear 2D-NMR techniques as well as by high-resolution mass spectrometry measurements. The absolute configuration of the asymmetric centers was studied by Marfey's method for HPLC. The stereochemistry of the asymmetric centers in tenuecyclamides A and B (1 and 2) could not be fully determined, while that of tenuecyclamides C and D (3 and 4) was unambiguously determined.