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通过顺序多组分反应构建的转模拟基于乙内酰脲的环。

Turn-Mimic Hydantoin-Based Loops Constructed by a Sequential Multicomponent Reaction.

作者信息

Caramiello Alessio Maria, Bellucci Maria Cristina, Marti-Rujas Javier, Sacchetti Alessandro, Volonterio Alessandro

机构信息

Department of Chemistry, Material and Chemical Engineering "Giulio Natta", Politecnico di Milano, via Mancinelli 7, Milano 20131, Italy.

Department of Food, Environmental and Nutritional Sciences, Università degli Studi di Milano, via Celoria 2, Milano 20133, Italy.

出版信息

J Org Chem. 2023 Nov 17;88(22):15790-15804. doi: 10.1021/acs.joc.3c01861. Epub 2023 Nov 6.

DOI:10.1021/acs.joc.3c01861
PMID:37932902
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10661056/
Abstract

A collection of peptidomimetics characterized by having an aspartic acid motif embedded in a rigid hydantoin heterocycle are synthesized through a sequential multicomponent domino process followed by standard regioselective deprotection/coupling reactions based on acid-base liquid/liquid purification protocols. H nuclear magnetic resonance experiments, molecular modeling, and X-ray analysis showed that the resulting hydantoin-based loops I (in particular) and II (to a lesser extent) can be considered novel β-turn inducer motifs being able to project two peptide-like strands in a U-shaped conformation driven by the formation of intermolecular hydrogen bonds.

摘要

通过连续多组分多米诺过程，随后基于酸碱液/液纯化方案进行标准区域选择性脱保护/偶联反应，合成了一组以嵌入刚性乙内酰脲杂环中的天冬氨酸基序为特征的拟肽。氢核磁共振实验、分子建模和X射线分析表明，所得基于乙内酰脲的环I（特别是）和环II（程度较小）可被视为新型β-转角诱导基序，能够通过分子间氢键的形成，以U形构象投射出两条肽样链。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7ad8/10661056/dbc829295cdc/jo3c01861_0011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7ad8/10661056/355ad673af91/jo3c01861_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7ad8/10661056/9d9e6a5dca87/jo3c01861_0012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7ad8/10661056/b42eddc01726/jo3c01861_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7ad8/10661056/2c8337818a54/jo3c01861_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7ad8/10661056/941d2a906db2/jo3c01861_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7ad8/10661056/f9f4f83162e7/jo3c01861_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7ad8/10661056/328d58c16d73/jo3c01861_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7ad8/10661056/31b7232bc422/jo3c01861_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7ad8/10661056/51fe57ebf72b/jo3c01861_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7ad8/10661056/3ddbd06542bd/jo3c01861_0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7ad8/10661056/640c35f4d1e8/jo3c01861_0010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7ad8/10661056/dbc829295cdc/jo3c01861_0011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7ad8/10661056/355ad673af91/jo3c01861_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7ad8/10661056/9d9e6a5dca87/jo3c01861_0012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7ad8/10661056/b42eddc01726/jo3c01861_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7ad8/10661056/2c8337818a54/jo3c01861_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7ad8/10661056/941d2a906db2/jo3c01861_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7ad8/10661056/f9f4f83162e7/jo3c01861_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7ad8/10661056/328d58c16d73/jo3c01861_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7ad8/10661056/31b7232bc422/jo3c01861_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7ad8/10661056/51fe57ebf72b/jo3c01861_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7ad8/10661056/3ddbd06542bd/jo3c01861_0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7ad8/10661056/640c35f4d1e8/jo3c01861_0010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7ad8/10661056/dbc829295cdc/jo3c01861_0011.jpg

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