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合成作为构象受限的免疫霉素类似物的哌啶核苷。

Synthesis of Piperidine Nucleosides as Conformationally Restricted Immucillin Mimics.

机构信息

Department of Chemical Sciences, University of Naples Federico II, Via Cintia, 80126 Naples, Italy.

Department of Chemical, Materials and Production Engineering, University of Naples Federico II, Piazzale V. Tecchio 80, 80125 Naples, Italy.

出版信息

Molecules. 2021 Mar 16;26(6):1652. doi: 10.3390/molecules26061652.

DOI:10.3390/molecules26061652
PMID:33809603
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8001838/
Abstract

The de novo synthesis of piperidine nucleosides from our homologating agent 5,6-dihydro-1,4-dithiin is herein reported. The structure and conformation of nucleosides were conceived to faithfully resemble the well-known nucleoside drugs Immucillins H and A in their bioactive conformation. NMR analysis of the synthesized compounds confirmed that they adopt an iminosugar conformation bearing the nucleobases and the hydroxyl groups in the appropriate orientation.

摘要

本文报道了从我们的同系物 5,6-二氢-1,4-二噻因出发从头合成哌啶核苷。核苷的结构和构象被设想为忠实地类似于众所周知的免疫球蛋白 H 和 A 核苷药物在其生物活性构象中。合成化合物的 NMR 分析证实,它们采用带有碱基和羟基的氨基糖构象,并以适当的取向排列。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/abca/8001838/8e41244336ae/molecules-26-01652-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/abca/8001838/a65a798b9ab4/molecules-26-01652-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/abca/8001838/82fb56421bb4/molecules-26-01652-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/abca/8001838/0013445f86c1/molecules-26-01652-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/abca/8001838/7491d648d3a0/molecules-26-01652-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/abca/8001838/8e41244336ae/molecules-26-01652-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/abca/8001838/a65a798b9ab4/molecules-26-01652-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/abca/8001838/82fb56421bb4/molecules-26-01652-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/abca/8001838/0013445f86c1/molecules-26-01652-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/abca/8001838/7491d648d3a0/molecules-26-01652-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/abca/8001838/8e41244336ae/molecules-26-01652-g003.jpg

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