Literature DB >> 28714148

Palladium(II)-Catalyzed Site-Selective C(sp3 )-H Alkynylation of Oligopeptides: A Linchpin Approach for Oligopeptide-Drug Conjugation.

Tao Liu1, Jennifer X Qiao2, Michael A Poss2, Jin-Quan Yu1.   

Abstract

The palladium(II)-catalyzed C(sp3 )-H alkynylation of oligopeptides was developed with tetrabutylammonium acetate as a key additive. Through molecular design, the acetylene motif served as a linchpin to introduce a broad range of carbonyl-containing pharmacophores onto oligopeptides, thus providing a chemical tool for the synthesis and modification of novel oligopeptide-pharmacophore conjugates by C-H functionalization. Dipeptide conjugates with coprostanol and estradiol were synthesized by this method for potential application in targeted drug delivery to tumor cells with overexpressed nuclear hormone receptors.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−H activation; alkynylation; drug conjugation; palladium; peptides

Mesh：

Substances：

Year:  2017        PMID： 28714148      PMCID： PMC5572133          DOI： 10.1002/anie.201706367

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  25 in total

1.  Modification of N-terminal α-amino groups of peptides and proteins using ketenes.

Authors:  Anna On-Yee Chan; Chi-Ming Ho; Hiu-Chi Chong; Yun-Chung Leung; Jie-Sheng Huang; Man-Kin Wong; Chi-Ming Che
Journal:  J Am Chem Soc       Date:  2012-01-30       Impact factor: 15.419

2.  Protein evolution with an expanded genetic code.

Authors:  Chang C Liu; Antha V Mack; Meng-Lin Tsao; Jeremy H Mills; Hyun Soo Lee; Hyeryun Choe; Michael Farzan; Peter G Schultz; Vaughn V Smider
Journal:  Proc Natl Acad Sci U S A       Date:  2008-11-11       Impact factor: 11.205

3.  Postsynthetic modification of peptides: chemoselective C-arylation of tryptophan residues.

Authors:  Javier Ruiz-Rodríguez; Fernando Albericio; Rodolfo Lavilla
Journal:  Chemistry       Date:  2010-01-25       Impact factor: 5.236

4.  Late-Stage Peptide Diversification by Bioorthogonal Catalytic C-H Arylation at 23 °C in H2 O.

Authors:  Yingjun Zhu; Michaela Bauer; Lutz Ackermann
Journal:  Chemistry       Date:  2015-06-02       Impact factor: 5.236

5.  Manganese-Catalyzed C-H Alkynylation: Expedient Peptide Synthesis and Modification.

Authors:  Zhixiong Ruan; Nicolas Sauermann; Elisabetta Manoni; Lutz Ackermann
Journal:  Angew Chem Int Ed Engl       Date:  2017-02-09       Impact factor: 15.336

6.  Site-specific introduction of an acetyl-lysine mimic into peptides and proteins by cysteine alkylation.

Authors:  Rong Huang; Marc A Holbert; Mary Katherine Tarrant; Sandrine Curtet; David R Colquhoun; Beverley M Dancy; Blair C Dancy; Yousang Hwang; Yong Tang; Katrina Meeth; Ronen Marmorstein; Robert N Cole; Saadi Khochbin; Philip A Cole
Journal:  J Am Chem Soc       Date:  2010-07-28       Impact factor: 15.419

7.  Selective Metal-Site-Guided Arylation of Proteins.

Authors:  Jens Willwacher; Ritu Raj; Shabaz Mohammed; Benjamin G Davis
Journal:  J Am Chem Soc       Date:  2016-07-12       Impact factor: 15.419

8.  N-methylation of peptides: a new perspective in medicinal chemistry.

Authors:  Jayanta Chatterjee; Chaim Gilon; Amnon Hoffman; Horst Kessler
Journal:  Acc Chem Res       Date:  2008-07-18       Impact factor: 22.384

9.  Cross-coupling of remote meta-C-H bonds directed by a U-shaped template.

Authors:  Li Wan; Navid Dastbaravardeh; Gang Li; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2013-11-20       Impact factor: 15.419

Review 10.  Targeting the androgen receptor with steroid conjugates.

Authors:  Paul M Levine; Michael J Garabedian; Kent Kirshenbaum
Journal:  J Med Chem       Date:  2014-07-08       Impact factor: 7.446
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  15 in total

1.  Utilizing Carbonyl Coordination of Native Amides for Palladium-Catalyzed C(sp3 )-H Olefination.

Authors:  Hojoon Park; Yang Li; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2019-07-04       Impact factor: 15.336

Review 2.  Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp3)-H Bonds.

Authors:  Bin Liu; Andrew M Romine; Camille Z Rubel; Keary M Engle; Bing-Feng Shi
Journal:  Chem Rev       Date:  2021-10-29       Impact factor: 60.622

3.  HSymM-guided engineering of the immunodominant p53 transactivation domain putative peptide antigen for improved binding to its anti-p53 monoclonal antibody.

Authors:  Zachary R Fritz; Rene S Schloss; Martin L Yarmush; Lawrence J Williams
Journal:  Bioorg Med Chem Lett       Date:  2021-08-26       Impact factor: 2.823

4.  Ligand Enabled Pd(II)-Catalyzed γ-C(sp3)-H Lactamization of Native Amides.

Authors:  Shuang Liu; Zhe Zhuang; Jennifer X Qiao; Kap-Sun Yeung; Shun Su; Emily C Cherney; Zheming Ruan; William R Ewing; Michael A Poss; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2021-12-16       Impact factor: 16.383

5.  Peptide-guided functionalization and macrocyclization of bioactive peptidosulfonamides by Pd(II)-catalyzed late-stage C-H activation.

Authors:  Jian Tang; Hongfei Chen; Yadong He; Wangjian Sheng; Qingqing Bai; Huan Wang
Journal:  Nat Commun       Date:  2018-08-23       Impact factor: 14.919

6.  Macrocyclization of peptidoarylacetamides with self-assembly properties through late-stage palladium-catalyzed C(sp2)▬H olefination.

Authors:  Jiantao Tan; Jie Wu; Shu Liu; Hequan Yao; Huan Wang
Journal:  Sci Adv       Date:  2019-03-08       Impact factor: 14.136

7.  Late-stage C(sp2)-H and C(sp3)-H glycosylation of C-aryl/alkyl glycopeptides: mechanistic insights and fluorescence labeling.

Authors:  Jun Wu; Nikolaos Kaplaneris; Shaofei Ni; Felix Kaltenhäuser; Lutz Ackermann
Journal:  Chem Sci       Date:  2020-03-24       Impact factor: 9.825

8.  Merging C(sp3)-H activation with DNA-encoding.

Authors:  Zhoulong Fan; Shuai Zhao; Tao Liu; Peng-Xiang Shen; Zi-Ning Cui; Zhe Zhuang; Qian Shao; Jason S Chen; Anokha S Ratnayake; Mark E Flanagan; Dominik K Kölmel; David W Piotrowski; Paul Richardson; Jin-Quan Yu
Journal:  Chem Sci       Date:  2020-09-07       Impact factor: 9.825

9.  Site-selective aqueous C-H acylation of tyrosine-containing oligopeptides with aldehydes.

Authors:  Marcos San Segundo; Arkaitz Correa
Journal:  Chem Sci       Date:  2020-10-06       Impact factor: 9.825

10.  Synthesis of amino acids and peptides with bulky side chains via ligand-enabled carboxylate-directed γ-C(sp3)-H arylation.

Authors:  Lei Liu; Yan-Hua Liu; Bing-Feng Shi
Journal:  Chem Sci       Date:  2019-11-11       Impact factor: 9.825
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