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使用N-杂环卡宾-铱(III)催化剂对未保护的α-氨基酸进行选择性定量N-官能化。

Selective quantitative N-functionalization of unprotected α-amino acids using NHC-Ir(III) catalyst.

作者信息

Saavedra Beatriz, Bermejo-López Aitor, Raeder Majken, Martín-Matute Belén

机构信息

Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 106 91 Stockholm, Sweden.

Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 106 91 Stockholm, Sweden.

出版信息

STAR Protoc. 2023 Mar 13;4(2):102147. doi: 10.1016/j.xpro.2023.102147.

DOI:10.1016/j.xpro.2023.102147
PMID:36920910
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10025274/
Abstract

Unnatural amino acids are valuable building blocks with numerous applications. Here, we present a quantitative technique for accessing mono-N-functionalized amino acids directly from unprotected substrates using alcohols as alkylating agents and an NHC-Ir(III) catalyst. We detail specific steps for catalyst preparation and application, as well as for catalyst recycling. The protocol excludes a few amino acids (l-cysteine, l-lysine, and l-arginine) and secondary alcohols. For complete details on the use and execution of this protocol, please refer to Bermejo-López et al. (2022)..

摘要

非天然氨基酸是具有众多应用的有价值的结构单元。在此，我们展示了一种定量技术，可使用醇类作为烷基化剂和NHC-Ir(III)催化剂，直接从未受保护的底物中获取单N-官能化氨基酸。我们详细说明了催化剂制备、应用以及催化剂循环利用的具体步骤。该方案排除了几种氨基酸（L-半胱氨酸、L-赖氨酸和L-精氨酸）和仲醇。有关此方案的使用和实施的完整详细信息，请参考Bermejo-López等人（2022年）的文献。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e8f4/10025274/0fbac022ed1a/gr12.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e8f4/10025274/775040d19a78/sc1.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e8f4/10025274/47f0ea29648e/gr3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e8f4/10025274/7832b09f7740/gr4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e8f4/10025274/f37371b116be/sc2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e8f4/10025274/d10bc619f70e/gr5.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e8f4/10025274/2c532fadb88b/gr7.jpg
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本文引用的文献

1
Biocatalytic Synthesis of Chiral N-Functionalized Amino Acids.手性 N-官能化氨基酸的生物催化合成。
Angew Chem Int Ed Engl. 2018 Oct 15;57(42):13821-13824. doi: 10.1002/anie.201806893. Epub 2018 Sep 21.
2
Direct N-alkylation of unprotected amino acids with alcohols.未保护的氨基酸与醇的直接N-烷基化反应。
Sci Adv. 2017 Dec 8;3(12):eaao6494. doi: 10.1126/sciadv.aao6494. eCollection 2017 Dec.
3
Micellization of true amphoteric surfactants.两性真表面活性剂的胶束化。
J Colloid Interface Sci. 2013 Dec 1;411:47-52. doi: 10.1016/j.jcis.2013.08.048. Epub 2013 Sep 10.
4
Catalysts based on amino acids for asymmetric reactions in water.基于氨基酸的用于水中不对称反应的催化剂。
Angew Chem Int Ed Engl. 2009;48(24):4288-97. doi: 10.1002/anie.200802038.
5
Nonclinical safety evaluation of muraglitazar, a novel PPARalpha/gamma agonist.新型PPARα/γ激动剂muraglitazar的非临床安全性评价
Toxicol Sci. 2007 Nov;100(1):248-58. doi: 10.1093/toxsci/kfm193. Epub 2007 Aug 4.
6
New uses of amino acids as chiral building blocks in organic synthesis.氨基酸作为手性砌块在有机合成中的新用途。
Org Lett. 2001 Oct 4;3(20):3119-20. doi: 10.1021/ol0164029.