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

Cyclic Hexapeptide Dimers, Antatollamides A and B, from the Ascidian Didemnum molle. A Tryptophan-Derived Auxiliary for l- and d-Amino Acid Assignments.
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DOI:
10.1021/acs.joc.7b01659
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发表时间:
2017-10-06
期刊:
The Journal of organic chemistry
影响因子:
--
通讯作者:
Molinski TF
Molinski TF
中科院分区:
其他
文献类型:
--
作者:
Salib MN;Molinski TF

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从采集于波恩佩的海鞘Didemnum molle中分离出两个二聚环六肽,antatollamides A(1)和B(2)。通过MS和1D和2D NMR数据的解释确定氨基酸组成和序列。安妥拉胺A的Raney Ni还原将二聚体裂解为相应的单体环状六肽,其中Cys被Ala取代。在完全水解后,通过用新的手性试剂(5-氟-2,4-二硝基苯基)-Nα-L-异丙胺(FDTA)(由L-Trp制备)衍生化,随后进行LCMS分析,确定了1的氨基酸构型;发现除D-Ala外,所有氨基酸均为L构型。
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)-Nα-L-tryptophanamide (FDTA), prepared from L-Trp, followed by LCMS analysis; all amino acids were found to be L-configured except for D-Ala.
DOI: 10.1021/acs.jnatprod.5b01125
发表时间: 2016-02-01
影响因子: 5.1
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