Cyclic Hexapeptide Dimers, Antatollamides A and B, from the Ascidian Didemnum molle. A Tryptophan-Derived Auxiliary for l- and d-Amino Acid Assignments,The Journal of Organic Chemistry

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Cyclic Hexapeptide Dimers, Antatollamides A and B, from the Ascidian Didemnum molle. A Tryptophan-Derived Auxiliary for l- and d-Amino Acid Assignments
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2017-09-18 00:00:00 , DOI: 10.1021/acs.joc.7b01659
Mariam N. Salib ₁ , Tadeusz F. Molinski ₁

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Two dimerized cyclic hexapeptides, antatollamides A (1) and B (2), were isolated from the colonial ascidian Didemnum molle collected in Pohnpei. The amino acid compositions and sequences were determined by interpretation of MS and 1D and 2D NMR data. Raney Ni reduction of antatollamide A cleaved the dimer to the corresponding monomeric cyclic hexapeptide with replacement of Cys by Ala. The amino acid configuration of 1 was established, after total hydrolysis, by derivatization with a new chiral reagent, (5-fluoro-2,4-dinitrophenyl)-N^α-l-tryptophanamide (FDTA), prepared from l-Trp, followed by LCMS analysis; all amino acids were found to be l-configured except for d-Ala.

中文翻译：

环状六肽二聚体，Antatollamides A和B，来自亚洲海Did。色氨酸衍生的辅助剂，用于l和d氨基酸分配

从Pohnpei收集的殖民地海鞘Didemnum molle中分离出两个二聚环六肽，antantallamides A（1）和B（2）。通过MS和1D和2D NMR数据的解释来确定氨基酸组成和序列。阮内镍还原antatollamide A的裂解成相应的单体环六肽的二聚体被Ala替换的Cys的该氨基酸结构1成立，总水解后，通过用新的手性试剂衍生化，（5-氟-2， 4-二硝基苯基） - ñ ^α -升-tryptophanamide（FDTA）中，从制备的升-Trp，随后通过LCMS分析; 发现所有氨基酸是l-除d -Ala外配置。

更新日期：2017-09-18

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