Facile synthesis of chiral 2-functionalized tetrahydroquinolines via Pd/Cu-catalyzed cascade γ-C(sp3)–H arylation/C–N coupling of amides derived from amino acids and their derivatives DOI

Dian Yu,

Siyuan Peng, Han Wang

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(17), P. 4388 - 4393

Published: Jan. 1, 2023

We successfully explored a one-pot strategy to synthesize valuable chiral 2-functionalized tetrahydroquinoline motifs through the precise modification of amides derived from commercially available natural amino acids.

Language: Английский

Postassembly Modification of Peptides by Histidine-Directed β-C(sp3)–H Arylation of Alanine at the Internal Positions: Overcoming the Inhibitory Effect of Peptide Bonds DOI
Sunday Adewale Akintelu, Qi Zhang, Bo Yao

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(18), P. 3991 - 3996

Published: May 1, 2024

Peptide modification by C(sp3)–H functionalization of residues at the internal positions remains underdeveloped due to inhibitory effect backbone amides. In this study, using histidine (His) as an endogenous directing group, we developed a novel method for β-C(sp3)–H alanine (Ala) diverse peptides. Through approach, wide range linear peptides were modified on side-chain Ala adjacent His afford functionalized in moderate good yield and excellent position selectivity. Furthermore, conjugation with functional molecules such glucuronide, oleanolic acid, dipeptide, fluorophore derivatives was achieved.

Language: Английский

Citations

6
Methionine-Enabled Peptides Modification through Late-stage Pd-catalyzed β-C(sp3)-H olefination/cyclization DOI

Fengjie Lu,

Xinyi Zhang,

Yujie Geng

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(61), P. 7942 - 7945

Published: Jan. 1, 2024

We present a method for site-selective diversification of peptides via Pd-catalyzed β-C(sp 3 )–H olefination/cyclization.

Language: Английский

Citations

3
Late-Stage Glycosylation of Peptides by Methionine-Directed β-C(sp3)–H Functionalization with 1-Iodoglycals DOI

Yunhao Ding,

Bo Yao

Organic Letters, Journal Year: 2024, Volume and Issue: 26(34), P. 7128 - 7133

Published: Aug. 19, 2024

Using l-methionine (Met) as the endogenous directing group, we developed Pd-catalyzed β-C(sp3)–H glycosylation of peptides with 1-iodoglycals. A wide range tri- to hexapeptides containing Ala-Met motifs underwent Ala C–H under standard conditions give glycopeptides smoothly. 15 proteinogenic amino acids (with easily removable protecting groups) were well tolerated. Control experiments indicated that Met acted a N,S-bidentate group and exhibited an effect superior other acid residues such l-aspartic (Asp), l-asparagine (Asn), S-protected l-cysteine (Cys). In addition, further transformation by HFIP-promoted 1,4-elimination furnished another type glycopeptide 1,3-diene motif, which provides handle for derivatization.

Language: Английский

Citations

3
Palladium-Catalyzed Intermolecular Functionalization of Unactivated Methylene C(sp3)—H Bonds DOI

Ming-Shun Mei,

Yanghui Zhang

Chinese Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 45(2), P. 620 - 620

Published: Jan. 1, 2025

Language: Английский

Citations

0
Design, Synthesis, and Application of Modified Linear Peptides as Potential Antidiabetic Agent DOI

Realy Behery,

Silvère Augustin Soavina,

Indrianasolo

et al.

Journal of Molecular Structure, Journal Year: 2025, Volume and Issue: unknown, P. 141970 - 141970

Published: March 1, 2025

Language: Английский

Citations

0
Endogenous group‐directed late‐stage C‐H functionalization of peptides DOI
Aman Singh Barahdia,

Karuna Thakare,

Lipat Kaur

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(13), P. 2844 - 2858

Published: May 18, 2024

Abstract Peptides are diverse in terms of their functional groups and side‐chain functionalities, late‐stage C−H functionalization plays a crucial role design. Approaches for such synthesis require pre‐installation post‐removal the directing group (DG). In recent times, chemical methods have been developed, focusing on external DG‐free peptides. These approaches utilize inherent native functionality peptides as DG to simplify synthetic routes, reducing steps, waste generation, enhancing sustainability, cost‐effectiveness, operational flexibility. Such facilitate both natural unnatural amino acid‐containing

Language: Английский

Citations

2
Ligand-Enabled, Cysteine-Directed β-C(sp3)–H Arylation of Alanine in Linear and Cyclic Peptides: Overcoming the Inhibitory Effect of Peptide Bonds DOI

Zhen-Lin Hou,

Yinian Tang,

Yu Lu

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(14), P. 11026 - 11033

Published: July 9, 2024

Language: Английский

Citations

2
Palladium-Catalyzed Enantioselective Directed C(sp3)–H Functionalization Using C5-Substituted 8-Aminoquinoline Auxiliaries DOI
Yi Huang,

Xiaoyan Lv,

Huarong Tong

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 26(1), P. 94 - 99

Published: Dec. 27, 2023

8-Aminoquinoline (AQ) has proven to be a highly effective bidentate directing group for palladium-catalyzed C–H functionalization reactions. However, enantiocontrol of AQ-directed C(sp3)–H reactions been challenging. Herein, new protocol is presented the Pd-catalyzed enantioselective arylation unactivated β bonds alkyl carboxamides with aryl iodides using C5-iodinated 8-aminoquinolines (IQ) auxiliary in conjugation BINOL ligand. Additionally, C5-aryl substituted 8-aminoquinoline can facilitate alkenylation and alkynylation benzylic 3-arylpropanamides corresponding bromide reagents under similar conditions.

Language: Английский

Citations

4
TAG‐Assisted Liquid‐Phase Synthesis and Structure Activity Relationship of Macolacin‐Based Side‐to‐Tail Cyclopeptides Antibiotic DOI
Haidi Li, Yuankui Jin,

Minfan Pei

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(22), P. 2728 - 2742

Published: July 12, 2024

Comprehensive Summary TAG‐assisted peptide synthesis technology enables optimal conservation of Fmoc amino acid raw materials and chemical solvents while eliminating the need for intricate chromatographic purification processes. This work presents a 4,4'‐diphenylphosphonoxy diphenylcarbinol tag‐mediated liquid‐phase approach preparing side‐to‐tail cyclopeptides macolacin which has strong activity against gram‐negative bacteria, its 15 analogues containing four N ‐methylation modified cyclopeptides, as well an investigation their structure‐activity relationship (SAR). The primarily focuses on modifications group Ile‐7 tail fatty acyl chain macolacin. incorporation , along with dihalogenated or monohalogenated benzoic acids modification, exhibited remarkable antibacterial efficacy minimal hepatocellular toxicity in vitro . present study identified ‐methylation‐modified antimicrobial cyclopeptide Ma14 that exhibits rapid bactericidal A. baumanii etc ., showing reduced toxicity. Molecular docking simulations were conducted to investigate binding outer membrane protein BamA baumannii findings demonstrated stable interactions then presented novel explain bacteriostatic mechanism macolacin‐based antibiotics.

Language: Английский

Citations

1
Facile synthesis of chiral 2-functionalized tetrahydroquinolines via Pd/Cu-catalyzed cascade γ-C(sp3)–H arylation/C–N coupling of amides derived from amino acids and their derivatives DOI

Dian Yu,

Siyuan Peng, Han Wang

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(17), P. 4388 - 4393

Published: Jan. 1, 2023

We successfully explored a one-pot strategy to synthesize valuable chiral 2-functionalized tetrahydroquinoline motifs through the precise modification of amides derived from commercially available natural amino acids.

Language: Английский

Citations

1