High-yield and high-purity amide bond formation using DMTMM PF6 for DNA-encoded libraries

被引：1

作者：

Hosozawa, Takumi ^{[1
]}

Niwa, Masatoshi ^{[1
]}

Takeuchi, Hisayuki ^{[1
]}

Inohana, Takehiko ^{[1
]}

Okumura, Kaori ^{[1
]}

Itoh, Shin ^{[1
]}

机构：

[1] Nissan Chem Corp, Chem Res Labs, Pharmaceut Res Dept, 10-1 Tsuboi Nishi 2 Chome, Funabashi, Chiba, Japan

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2024年 / 110卷

关键词：

DNA-encoded libraries (DELs); Amidation reaction; Sterically hindered amines and carboxylic acids; DMTMMPF6; on-DNA;

D O I：

10.1016/j.bmcl.2024.129859

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

In this study, we report on the ability of DMTMM PF6 to improve the amidation reaction. The on-DNA amidation reaction using DMTMM PF6 demonstrates higher conversion rates than those using HATU or DMTMM Cl, particularly with challenging sterically hindered amines and carboxylic acids. The developed method enables the expansion of available building blocks and the efficient synthesis of high-purity DNA-encoded libraries.

引用

页数：5

共 38 条

[1] Macrocyclizing DNA-Linked Peptides via Three-Component Cyclization and Photoinduced Chemistry
Bao, Yandan
Xing, Minyan
Matthew, Naylor
Chen, Xiaohua
Wang, Xuan
Lu, Xiaojie
[J]. ORGANIC LETTERS, 2023, 26 (14) : 2763 - 2767
[2] ENCODED COMBINATORIAL CHEMISTRY
BRENNER, S
LERNER, RA
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1992, 89 (12) : 5381 - 5383
[3] Synthesis of a DNA-Encoded Macrocyclic Library Utilizing Intramolecular Benzimidazole Formation
Chai, Jing
Arico-Muendel, Christopher C.
Ding, Yun
Pollastri, Michael P.
Scott, Sarah
Mantell, Mark A.
Yao, Gang
[J]. BIOCONJUGATE CHEMISTRY, 2023, 34 (06) : 988 - 993
[4] Factors Determining the Selection of Organic Reactions by Medicinal Chemists and the Use of These Reactions in Arrays (Small Focused Libraries)
Cooper, Tony W. J.
Campbell, Ian B.
Macdonald, Simon J. F.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (44) : 8082 - 8091
[5] Novel Autotaxin Inhibitor for the Treatment of Idiopathic Pulmonary Fibrosis: A Clinical Candidate Discovered Using DNA-Encoded Chemistry
Cuozzo, John W.
Clark, Matthew A.
Keefe, Anthony D.
Kohlmann, Anna
Mulvihill, Mark
Ni, Haihong
Renzetti, Louis M.
Resnicow, Daniel, I
Ruebsam, Frank
Sigel, Eric A.
Thomson, Heather A.
Wang, Ce
Xie, Zhifeng
Zhang, Ying
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2020, 63 (14) : 7840 - 7856
[6] Chemical composition of DNA-encoded libraries, past present and future
Dickson, Paige
Kodadek, Thomas
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (19) : 4676 - 4688
[7] Synthesis of DNA-Encoded Macrocyclic Peptides via Nitrile-Aminothiol Click Reaction
Fan, Lijun
Yu, Yang
Jayne, Charles
Frost, John R.
Scott, Jack D.
[J]. ORGANIC LETTERS, 2023, 25 (44) : 8038 - 8042
[8] DNA-Encoded Chemistry: Drug Discovery from a Few Good Reactions
Fitzgerald, Patrick R.
Paegel, Brian M.
[J]. CHEMICAL REVIEWS, 2021, 121 (12) : 7155 - 7177
[9] Systematic Evaluation and Optimization of Modification Reactions of Oligonucleotides with Amines and Carboxylic Acids for the Synthesis of DNA-Encoded Chemical Libraries
Franzini, Raphael M.
Samain, Florent
Abd Elrahman, Maaly
Mikutis, Gediminas
Nauer, Angela
Zimmermann, Mauro
Scheuermann, Joerg
Hall, Jonathan
Neri, Dario
[J]. BIOCONJUGATE CHEMISTRY, 2014, 25 (08) : 1453 - 1461
[10] DNA-Encoded Chemical Libraries: A Comprehensive Review with Succesful Stories and Future Challenges
Gironda-Martinez, Adrian
Donckele, Etienne J.
Samain, Florent
Neri, Dario
[J]. ACS PHARMACOLOGY & TRANSLATIONAL SCIENCE, 2021, 4 (04) : 1265 - 1279

← 1 2 3 4 →