Mutremdamide A and koshikamides C-H, peptide inhibitors of HIV-1 entry from different Theonella species.
Mutremdamide A and koshikamides C-H, peptide inhibitors of HIV-1 entry from different Theonella species.
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DOI：
10.1021/jo100076g
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发表时间：
2010-07-02
期刊：
影响因子：
--
通讯作者：
Bewley CA
中科院分区：
文献类型：
--
作者：
Plaza A;Bifulco G;Masullo M;Lloyd JR;Keffer JL;Colin PL;Hooper JN;Bell LJ;Bewley CA
从西尼罗和西奥尼拉的不同深水标本中分离得到一个新的硫酸盐化环多肽，命名为MutreDamide A，以及6个新的高度N-甲基化的多肽，命名为Koshikamdes C-H。它们的结构通过广泛的2D核磁共振、ESI或CDESI和QTOF-MS/MS实验以及通过量子力学计算、改进的Marfey方法和手性高效液相色谱确定的绝对构型来确定。Mutreamide A显示了一种稀有的2-氨基-3-(2-羟基苯基)丙酸和一种新的N-δ-氨基甲酰-β-磺化天冬酰胺。Koshikamide C-E是线性十一肽，Koshikamide F-H是含有10个残基的大内酯的17个残基的脱肽。Koshikamide F和G不同于B和H的部分原因是共轭单元2-(3-amino-5-oxopyrrolidin-2-ylidene)propanoic酸的存在。环状Koshikamide F和H在低微摩尔浓度下抑制HIV-1进入，而它们的线性对应物不起作用。这里研究的Theonella集合的特点是MutreDamide A、Koshikamide和Theonellamide的共同出现，它们的组合似乎定义了一种新的Theonella化学型，可以在更深的水域中发现。
A new sulfated cyclic depsipeptide, termed mutremdamide A, and six new highly N-methylated peptides, termed koshikamides C–H, were isolated from different deep-water specimens of Theonella swinhoei and Theonella cupola. Their structures were determined using extensive 2D NMR, ESI, or CDESI and QTOF-MS/MS experiments and absolute configurations established by quantum mechanical calculations, advanced Marfey's method, and chiral HPLC. Mutremdamide A displays a rare 2-amino-3-(2-hydroxyphenyl)propanoic acid and a new Nδ-carbamoyl-β-sulfated asparagine. Koshikamides C–E are linear undecapeptides, and koshikamides F–H are 17-residue depsipeptides containing a 10-residue macrolactone. Koshikamides F and G differ from B and H in part by the presence of the conjugated unit 2-(3-amino-5-oxopyrrolidin-2-ylidene)propanoic acid. Cyclic koshikamides F and H inhibited HIV-1 entry at low micromolar concentrations while their linear counterparts were inactive. The Theonella collections studied here are distinguished by co-occurrence of mutremdamide A, koshikamides, and theonellamides, the combination of which appears to define a new Theonella chemotype that can be found in deeper waters.
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影响因子：
3.6
作者：
Araki, Takahiro;Matsunaga, Shigeki;Fusetani, Nobuhiro
通讯作者：
Fusetani, Nobuhiro
影响因子：
5.1
作者：
Murphy, Annabel C.;Mitova, Maya I.;Munro, Murray H. G.
通讯作者：
Munro, Murray H. G.
影响因子：
3.6
作者：
Matsumori, N;Kaneno, D;Tachibana, K
通讯作者：
Tachibana, K
影响因子：
5.2
作者：
Bifulco, G;Bassarello, C;Gomez-Paloma, L
通讯作者：
Gomez-Paloma, L
影响因子：
5.1
作者：
Plaza, Alberto;Gustchina, Elena;Bewley, Carole A.
通讯作者：
Bewley, Carole A.