Recent advances in γ-C(sp3)–H bond activation of amides, aliphatic amines, sulfanilamides and amino acids

2022 ◽  
Vol 455 ◽  
pp. 214255
Shao-Fei Ni ◽  
Guanglong Huang ◽  
Yonghui Chen ◽  
James S. Wright ◽  
Mingde Li ◽  
2019 ◽  
Yongzheng Ding ◽  
Shuai Fan ◽  
Xiaoxi Chen ◽  
yuzhen gao ◽  
Gang Li

A Pdᴵᴵ-catalyzed, ligand-enabled gamma-C(sp3)–H arylation of free primary aliphatic amines and amino esters without using an exogenous directing group is reported. This reaction is compatible with unhindered free aliphatic amines, and it is also be applicable to the rapid synthesis of biologically and synthetically valuable unnatural α-amino acids. Large scale synthesis is also feasible using this method.<br>

Synlett ◽  
2019 ◽  
Vol 30 (11) ◽  
pp. 1289-1302 ◽  
Phil Servatius ◽  
Lukas Junk ◽  
Uli Kazmaier

Peptide modifications via C–C bond formation have emerged as valuable tools for the preparation and alteration of non-proteinogenic amino acids and the corresponding peptides. Modification of glycine subunits in peptides allows for the incorporation of unusual side chains, often in a highly stereoselective manner, orchestrated by the chiral peptide backbone. Moreover, modifications of peptides are not limited to the peptidic backbone. Many side-chain modifications, not only by variation of existing functional groups, but also by C–H functionalization, have been developed over the past decade. This account highlights the synthetic contributions made by our group and others to the field of peptide modifications and their application in natural product syntheses.1 Introduction2 Peptide Backbone Modifications via Peptide Enolates2.1 Chelate Enolate Claisen Rearrangements2.2 Allylic Alkylations2.3 Miscellaneous Modifications3 Side-Chain Modifications3.1 C–H Activation3.1.1 Functionalization via Csp3–H Bond Activation3.2.2 Functionalization via Csp2–H Bond Activation3.2 On Peptide Tryptophan Syntheses4 Conclusion

Molecules ◽  
2020 ◽  
Vol 25 (22) ◽  
pp. 5270
Zhenbo Yuan ◽  
Xuanzhong Liu ◽  
Changmei Liu ◽  
Yan Zhang ◽  
Yijian Rao

Non-proteinogenic amino acids have attracted tremendous interest for their essential applications in the realm of biology and chemistry. Recently, rising C–H functionalization has been considered an alternative powerful method for the direct synthesis of non-proteinogenic amino acids. Meanwhile, photochemistry has become popular for its predominant advantages of mild conditions and conservation of energy. Therefore, C–H functionalization and photochemistry have been merged to synthesize diverse non-proteinogenic amino acids in a mild and environmentally friendly way. In this review, the recent developments in the photo-mediated C–H functionalization of proteinogenic amino acids derivatives for the rapid synthesis of versatile non-proteinogenic amino acids are presented. Moreover, postulated mechanisms are also described wherever needed.

Excitotoxins ◽  
1983 ◽  
pp. 43-54 ◽  
J. Davies ◽  
R. H. Evans ◽  
A. W. Jones ◽  
K. N. Mewett ◽  
D. A. S. Smith ◽  

ChemInform ◽  
2007 ◽  
Vol 38 (48) ◽  
Qun Jiang ◽  
Deshou Jiang ◽  
Yuyang Jiang ◽  
Hua Fu ◽  
Yufen Zhao

Molecules ◽  
2020 ◽  
Vol 25 (18) ◽  
pp. 4216
Héctor Martínez Pérez-Cejuela ◽  
José Manuel Herrero-Martínez ◽  
Ernesto F. Simó-Alfonso

This review summarizes the recent advances concerning metal–organic frameworks (MOFs) modified with several biomolecules (e.g., amino acids, nucleobases, proteins, antibodies, aptamers, etc.) as ligands to prepare affinity-based sorbents for application in the sample preparation field. The preparation and incorporation strategies of these MOF-based affinity materials were described. Additionally, the different types of ligands that can be employed for the synthesis of these biocomposites and their application as sorbents for the selective extraction of molecules and clean-up of complex real samples is reported. The most important features of the developed biocomposites will be discussed throughout the text in different sections, and several examples will be also commented on in detail.

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