Methionine-enabled peptide modification through late-stage Pd-catalyzed β-C (sp 3)–H olefination/cyclization

F Lu, X Zhang, Y Geng, H Wang, J Tang - Chemical Communications, 2024 - pubs.rsc.org
We present a method for site-selective diversification of peptides via Pd-catalyzed β-C (sp3)–
H olefination/cyclization. In this protocol, the native methionine residue acts as a directing …

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

ZL Hou, Y Tang, Y Lu, B Yao - ACS Catalysis, 2024 - ACS Publications
Peptide modification by coordination-assisted C (sp3)–H functionalization on the aliphatic
side chains of residues at the internal positions remains underdeveloped because of the …

Palladium-Catalyzed Enantioselective Directed C(sp3)–H Functionalization Using C5-Substituted 8-Aminoquinoline Auxiliaries

Y Huang, X Lv, HR Tong, W He, Z Bai, H Wang… - Organic …, 2023 - ACS Publications
8-Aminoquinoline (AQ) has proven to be a highly effective bidentate directing group for
palladium-catalyzed C–H functionalization reactions. However, enantiocontrol of AQ …

Endogenous Group‐Directed Late‐Stage C− H Functionalization of Peptides

AS Barahdia, KL Thakare, L Kaur… - Advanced Synthesis & …, 2024 - Wiley Online Library
Peptides are diverse in terms of their functional groups and side‐chain functionalities, and
late‐stage C− H functionalization plays a crucial role in their design. Approaches for such …

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

Y Ding, B Yao - Organic Letters, 2024 - ACS Publications
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 of tri-to hexapeptides …

Postassembly Modification of Peptides by Histidine-Directed β-C(sp3)–H Arylation of Alanine at the Internal Positions: Overcoming the Inhibitory Effect of Peptide …

SA Akintelu, Q Zhang, B Yao - Organic Letters, 2024 - ACS Publications
Peptide modification by C (sp3)–H functionalization of residues at the internal positions
remains underdeveloped due to the inhibitory effect of backbone amides. In this study, using …

Facile synthesis of chiral 2-functionalized tetrahydroquinolines via Pd/Cu-catalyzed cascade γ-C (sp 3)–H arylation/C–N coupling of amides derived from amino acids …

D Yu, SY Peng, H Wang, QC Zheng, YH Ma… - Organic Chemistry …, 2023 - pubs.rsc.org
In this work, we explored the precise modification of amides derived from commercially
available natural amino acids and their derivatives via Pd/Cu-catalyzed cascade γ-C (sp3) …

TAG‐Assisted Liquid‐Phase Synthesis and Structure Activity Relationship of Macolacin‐Based Side‐to‐Tail Cyclopeptides Antibiotic

H Li, Y Jin, M Pei, L Zhang, L Wang… - Chinese Journal of …, 2024 - Wiley Online Library
Comprehensive Summary TAG‐assisted peptide synthesis technology enables optimal
conservation of Fmoc amino acid raw materials and chemical solvents while eliminating the …

Late‐Stage Pd (II)‐Catalyzed C (sp3)− H Functionalization of Peptides Directed by a Removable, Backbone‐Inserted Amidoxime Ether

Y Wu, B Zhu, H Fan, H Bernard… - Angewandte Chemie … - Wiley Online Library
Palladium (II)‐catalyzed C–H functionalization has attracted considerable attention as a
pathway to late‐stage modification of peptides. Herein, we report the Pd‐catalyzed C (sp3) …

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

M Mei, Y Zhang - Chinese Journal of Organic Chemistry - sioc-journal.cn
Although transition metal-catalyzed methylene C (sp 3)-H functionalization is a great
challenge, it has made noticeable progress in recent years. This review specifically …