Institute for Molecular Bioscience, The University of Queensland , St Lucia, Queensland 4072, Australia.
Org Lett. 2018 Jan 19;20(2):377-380. doi: 10.1021/acs.orglett.7b03666. Epub 2018 Jan 9.
A rice cultivation of a fish gastrointestinal tract-derived fungus, Trichoderma sp. CMB-F563, yielded natural products incorporating a rare hydrazine moiety, embedded within a Schiff base. Structures inclusive of absolute configurations were assigned to prolinimines A-D (1-4) on the basis of detailed spectroscopic and C Marfey's analysis, as well as biosynthetic considerations, biomimetic total synthesis, and chemical transformations. Of note, monomeric 1 proved to be acid labile and, during isolation, underwent quantitative transformation to dimeric 3 and trimeric 4. Prolinimines are only the second reported natural products incorporating an N-amino-Pro residue, the first to include l-Pro, the first to occur as Schiff bases, and the first to be isolated from a microorganism.
一种鱼类胃肠道来源的真菌，即木霉属 CMB-F563 的水稻栽培，产生了天然产物，其中包含一个罕见的腙部分，嵌入一个席夫碱中。基于详细的光谱和 C Marfey 分析以及生物合成考虑、仿生全合成和化学转化，确定脯氨酸 A-D（1-4）的结构包括绝对构型。值得注意的是，单体 1 被证明是酸不稳定的，并且在分离过程中经历了定量转化为二聚体 3 和三聚体 4。脯氨酸是仅有的第二个报道的包含 N-氨基-Pro 残基的天然产物，第一个包含 l-Pro，第一个作为席夫碱存在，并且是第一个从微生物中分离出来的。
