CCL

CCL 2018 29( 07) Published: 22 July 2018

Editorial

15^th Chinese International Peptide Symposium

Xuechen Li, Lei Liu, Yanmei Li

CCL 2018 Vol. 29 (07): 999-1000 DOI:10.1016/j.cclet.2018.06.004

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Reviews

Transition-metal-catalyzed C-H functionalization for late-stage modification of peptides and proteins

Xi Lu, Shi-Jiang He, Wan-Min Cheng, Jing Shi

CCL 2018 Vol. 29 (07): 1001-1008 DOI:10.1016/j.cclet.2018.05.011

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The present review surveyed the progress achieved in the late-stage modification of peptides and proteins utilizing transition- metal-catalyzed C—H functionalization with C—C and C—X (F, Cl, O, N, B, etc.) bonds formation.

Recent advances in enzyme-mediated peptide ligation

Silin Xu, Zhenguang Zhao, Junfeng Zhao

CCL 2018 Vol. 29 (07): 1009-1016 DOI:10.1016/j.cclet.2018.05.024

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Artificial synthesis and site-specific modification of peptides and proteins have evolved into an indispensable tool for protein engineers and chemical biologists. Chemical and enzymatic approaches to peptide ligation are important alternatives of recombinant DNA technology for protein synthesis and modification. In the past decades, several natural peptide ligases have been discovered. Additionally, protein engineering for improving the ligation efficiencies of the natural peptide ligase and reversing the functionality of protease have provided more powerful peptide ligases. Herein, we briefly summarized the advances of enzyme-mediated peptide ligation and their application in protein synthesis and modification.

A mini-review on the enzyme-mediated manipulation of proteins/peptides

Shaomin Lin, Chunmao He

CCL 2018 Vol. 29 (07): 1017-1021 DOI:10.1016/j.cclet.2018.05.006

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A number of enzymes are available in the toolbox facilitating the site-selective labeling, ligation, cyclization of proteins or peptides. In this review, some of the most important enzymes were discussed.

Discovery and biosynthesis of thioviridamide-like compounds

Jian Tang, Jingxia Lu, Qunfeng Luo, Huan Wang

CCL 2018 Vol. 29 (07): 1022-1028 DOI:10.1016/j.cclet.2018.05.004

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Thioviridamide-like compounds are a unique subfamily of ribosomally synthesized and post-translationally modified peptide and contain characteristic thioamide bonds and S-[(Z)-2-aminovinyl]-D-cysteine (AviCys). Members of this family are active against a number of cancer cell lines. As a unique subgroup of RiPPs, the distribution, biosynthetic machinery and the mode of action of thioviridamide and related compounds remain largely unknown. In this review, we outlined recent advances in the discovery of thioviridamide-like peptide natural products and the effort in the elucidation of their biosynthetic origin.

Distribution of micropeptide-coding sORFs in transcripts

Xinqiang Yin, Jialiang Hu, Hanmei Xu

CCL 2018 Vol. 29 (07): 1029-1032 DOI:10.1016/j.cclet.2018.04.027

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Many translated sORFs have been identified across mRNAs, including 5'-upstream, coding domain, and 3'-downstream. sORFs have also been found in circular RNAs, pri-miRNAs, and ribosomal RNAs. Here, we presented an overview of the wide distribution of the sORFs in transcripts and their functional roles in organisms.

Discovery, structure, and chemical synthesis of disulfide-rich peptide toxins and their analogs

Ge-Min Fang, Xiao-Xu Chen, Qian-Qian Yang, Liang-Jing Zhu, Ning-Ning Li, Hai-Zhu Yu, Xiang-Ming Meng

CCL 2018 Vol. 29 (07): 1033-1042 DOI:10.1016/j.cclet.2018.02.002

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Disulfide bond-rich peptide toxins are promising scaffolds for the development of medicinal peptides because they possess a rigid 3D structure formed by multiple disulfide bonds. In this review, we discussed recent advances in the discovery, structural elucidation and chemical synthesis of disulfide-rich peptide toxins and their analogs.

Synthesis of Ras proteins and their application in biofunctional studies

Jun Hu, Pengcheng Zhu, Yanmei Li, Yongxiang Chen

CCL 2018 Vol. 29 (07): 1043-1050 DOI:10.1016/j.cclet.2018.05.035

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We summarized the developed strategies including chemical total synthesis, biosynthesis and semi-synthesis for producing Ras proteins with modification and their application in biological studies.

Peptide-based approaches to identify and characterize proteins that recognize histone post-translational modifications

Jianwei Lin, Xiang David Li

CCL 2018 Vol. 29 (07): 1051-1057 DOI:10.1016/j.cclet.2018.05.017

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In this review, we summarize the development and applications of synthetic peptide based tools to identify and characterize binding proteins of histone posttranslational modifications (PTMs). The limitation of peptide-based approaches is then discussed, followed by a brief description on recent development of nucleosome-based tools.

Peptide photocaging: A brief account of the chemistry and biological applications

Wing Ho So, Clarence T. T. Wong, Jiang Xia

CCL 2018 Vol. 29 (07): 1058-1062 DOI:10.1016/j.cclet.2018.05.015

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In this mini-review, we summarized the state-of-the-art development of photo-protecting groups for peptide photocaging including the un-caging mechanism of different PPGs, the synthesis of photo-caged peptides, and the recent applications of peptide photocaging in chemical biology.

A mini-review and perspective on multicyclic peptide mimics of antibodies

Weidong Liu, Chuanliu Wu

CCL 2018 Vol. 29 (07): 1063-1066 DOI:10.1016/j.cclet.2018.03.015

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This review gave a brief introduction on recent development in monocyclic and multicyclic peptide mimics of antibodies and provides a perspective on screening and design of multicyclic peptide mimics of antibodies in the future.

Macrocyclic peptides as regulators of protein-protein interactions

Yang Jiang, Hongyi Long, Yujie Zhu, Yi Zeng

CCL 2018 Vol. 29 (07): 1067-1073 DOI:10.1016/j.cclet.2018.05.028

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Protein-protein interactions are attractive but challenging targets for drug discovery. Recent technological progress and examples using macrocyclic peptides as protein interaction modulators are reviewed.

Methods for engineering therapeutic peptides

Yaohao Li, Kimberly A. Clark, Zhongping Tan

CCL 2018 Vol. 29 (07): 1074-1078 DOI:10.1016/j.cclet.2018.05.027

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This review discussed recent advancements related to therapeutic peptide engineering.

The application of sulfur-containing peptides in drug discovery

Jiaoyan Zhao, Xuefeng Jiang

CCL 2018 Vol. 29 (07): 1079-1087 DOI:10.1016/j.cclet.2018.05.026

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The purpose of the present review is to focus on the discovery of various sulfur-containing peptides with particular emphasis on their pharmacological mechanisms. This presentation is organized according to the structures of the sulfur-containing peptides.

Different stapling-based peptide drug design: Mimicking α-helix as inhibitors of protein-protein interaction

Xiang Li, Yan Zou, Hong-Gang Hu

CCL 2018 Vol. 29 (07): 1088-1092 DOI:10.1016/j.cclet.2018.01.018

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We category and analyze key examples of various peptide stapling strategies based on different cross-links aligned on the side chain of peptides mainly in the last three years.

Recent development on peptide-based probes for multifunctional biomedical imaging

Yuling Xu, Mei Tian, Hong Zhang, Yuling Xiao, Xuechuan Hong, Yao Sun

CCL 2018 Vol. 29 (07): 1093-1097 DOI:10.1016/j.cclet.2018.03.032

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Peptide-based probes play prominent roles in biomedical research due to their promising properties such as high biocompatibility, fast excretion, favorable pharmacokinetics as well as easy and robust preparation. Considering the translation of imaging probes into clinical applications, peptide-based probes remain to be the most desirable and optimal candidates.

Photosensitive peptide hydrogels as smart materials for applications

Dongdong Wu, Xian Xie, Adnan A. Kadi, Yan Zhang

CCL 2018 Vol. 29 (07): 1098-1104 DOI:10.1016/j.cclet.2018.04.030

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Photosensitive supramolecular peptide hydrogels with the gelators forming by the integration of photosensitive moieties and peptides have been briefly summarized the hydrogelation capabilities, the expressing manner serving as smart materials, and practical applications.

Programmable pyrrole-imidazole polyamides: A potent tool for DNA targeting

Chunlei Wu, Wei Wang, Lijing Fang, Wu Su

CCL 2018 Vol. 29 (07): 1105-1112 DOI:10.1016/j.cclet.2018.05.025

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Pyrrole-imidazole (Py-Im) polyamides are a class of programmable minor-groove binders that recognize pre-determined DNA double helixes with high affinity and specificity. This review summarized the recent advances of Py-Im polyamides from their synthesis to applications via various modifications at the molecular level.

Communications

Efficient preparation of β-hydroxy aspartic acid and its derivatives

Long Liu, Bo Wang, Cheng Bi, Gang He, Gong Chen

CCL 2018 Vol. 29 (07): 1113-1115 DOI:10.1016/j.cclet.2018.05.012

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We reported an efficient and practical synthetic route to various properly-protected erythreo-β-OH-Asp compounds, which are key β-branched a-amino acid units in coralmycin A and other peptide natural products.

Enzymatic clickable functionalization of peptides via computationally engineered peptide amidase

Tong Zhu, Lu Song, Ruifeng Li, Bian Wu

CCL 2018 Vol. 29 (07): 1116-1118 DOI:10.1016/j.cclet.2018.03.033

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The computationally engineered peptide amidase exhibits great promising potential in the C-terminal modification of peptides using prop-2-yn-1-amine (PYA) or prop-2-en-1-amine (PEA) as the nucleophile. Subsequently, modified peptides could be further functionalized via click reaction without elaborate isolation of the intermediate.

Development of aspartic acid ligation for peptide cyclization derived from serine/threonine ligation

Ci Xu, Jianchao Xu, Han Liu, Xuechen Li

CCL 2018 Vol. 29 (07): 1119-1122 DOI:10.1016/j.cclet.2018.03.012

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Based on a mechanism analogous to the serine/threonine ligation, the aspartic acid ligation, which is facilitated by the γ-amino alcohol based ligation and oxidation, is developed and applied to the synthesis of cyclic peptides. The γ-hydroxyl group triggers the ring-chain tautomerization via a 6-endo-trig process, while the δ-hydroxyl group facilitates the oxidative cleavage of the vicinal diol to give carboxylic acid.

On-resin peptide ligation via C-terminus benzyl ester

Bin Zhou, Faridoon, Xiaobo Tian, Jian Li, Dongliang Guan, Xing Zheng, Yu Guo, Wei Huang

CCL 2018 Vol. 29 (07): 1123-1126 DOI:10.1016/j.cclet.2018.03.021

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Here, we reported a new approach of on-resin peptide ligation using C-terminal benzyl ester as the stabilized precursor of thioester, which enables both N-terminal elongation and C-terminal peptide ligation on a Rink Amide resin.

Glycopeptide ligation via direct aminolysis of selenoester

Jing-Jing Du, Ling-Ming Xin, Ze Lei, Shi-Yao Zou, Wen-Bo Xu, Chang-Wei Wang, Lian Zhang, Xiao-Fei Gao, Jun Guo

CCL 2018 Vol. 29 (07): 1127-1130 DOI:10.1016/j.cclet.2018.04.016

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In this work, the selenoester of unprotected glycopeptide was readily prepared, and the direct aminolysis of glycopeptide selenoester was successfully applied to synthesize MUC1 mucin sequence.

Synthetic studies toward human interleukin-5

Jinrong Liu, Suwei Dong

CCL 2018 Vol. 29 (07): 1131-1134 DOI:10.1016/j.cclet.2018.05.014

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Disulfide-reduced form of IL-5 is assembled from three peptide segments in the N to C direction. Reconstitution of the protein under different folding conditions has also been investigated.

Chemical synthesis and structural analysis of guanylate cyclase C agonist linaclotide

Chenchen Chen, Shuai Gao, Qian Qu, Pengcheng Mi, Anjin Tao, Yi-Ming Li

CCL 2018 Vol. 29 (07): 1135-1138 DOI:10.1016/j.cclet.2018.01.005

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Linaclotide and its D-enantiomer were obtained through Fmoc solid phase peptide synthesis method and co-crystalized through racemic crystallization. The crystal structure showed that linaclotide has a tight, three-beta turns structure immobilized by three pairs of disulfide bonds.

Total synthesis of snake toxin a-bungarotoxin and its analogues by hydrazide-based native chemical ligation

Xiao-Qi Guo, Jun Liang, Ying Li, Yong Zhang, Dongliang Huang, Changlin Tian

CCL 2018 Vol. 29 (07): 1139-1142 DOI:10.1016/j.cclet.2018.05.005

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A new method for α-bungarotoxin was reported by combining Fmoc-SPPS and peptide hydrazide based ligat ion strategy.

Synthesis of cyclic peptide reniochalistatin E and conformational isomers

Huiyun Luo, Hongli Yin, Chaojun Tang, Ping Wang, Feng Liang

CCL 2018 Vol. 29 (07): 1143-1146 DOI:10.1016/j.cclet.2018.05.033

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Here we describe a convergent synthesis of reniochalistatin E that utilized solid-phase peptide synthesis. For macrolactamization of the linear peptides without the side chain protecting group, we obtained reniochalistatin E and its conformational isomers with 32% isolation yield.

A proximity-induced covalent fluorescent probe for selective detection of bromodomain 4

Ling Feng, Mohit Chhabra, Wing Ho So, Qing Zhu, Jiang Xia, Hongyan Sun

CCL 2018 Vol. 29 (07): 1147-1150 DOI:10.1016/j.cclet.2018.05.031

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Through proximity-induced conjugation reaction, a peptide-based fluorescent probe was designed and synthesized for selective detection of bromodomain 4.

A study of the lipid-mediated dimerization of the RAGE TM+JM domains by molecular dynamic simulations

Jialin Chen, Fude Sun, Peng Chen, Mengya Chai, Lida Xu, Shi-Zhong Luo

CCL 2018 Vol. 29 (07): 1151-1154 DOI:10.1016/j.cclet.2018.04.005

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We further emphasized the key roles of the A342xxxG346xxG349xxxT353xxL356xxxV360 motif in the left-handed configuration and the L345xxxG349xxG352xxxL356 motif in the right-handed configuration. In addition, we revealed that the juxtamembrane (JM) domain within A375 could determine the RAGE TM dimeric structure. Overall, we provide the molecular.

Biochemical properties of K_11,48-branched ubiquitin chains

Lu-Jun Liang, Yanyan Si, Shan Tang, Dongliang Huang, Zhipeng A. Wang, Changlin Tian, Ji-Shen Zheng

CCL 2018 Vol. 29 (07): 1155-1159 DOI:10.1016/j.cclet.2018.03.022

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The affinities of chemically synthetic linkage- and length-defined K_11,48-branched ubiquitin chains binding to ubiquitin receptor S5a were quantitatively measured. Proteasome-associated deubiquitinase Rpn11 showed a higher activity towards K_11,48-branched ubiquitin chains.

Development of a potent peptide inhibitor of estrogen receptor α

Xuan Qin, Hui Zhao, Yanhong Jiang, Feng Yin, Yuan Tian, Mingsheng Xie, Xiyang Ye, Naihan Xu, Zigang Li

CCL 2018 Vol. 29 (07): 1160-1162 DOI:10.1016/j.cclet.2018.04.004

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A potent peptide inhibitor of estrogen receptor α (ER-α) with significantly increased cellular uptake and cellular distribution was developed by cell penetrating peptide attachment. The resulted peptide conjugate showed selective toxicity towards estrogen receptor positive cell lines and induced decreased transcription of estrogen receptor α downstream genes.

Effects of linker amino acids on the potency and selectivity of dimeric antimicrobial peptides

Ming Kai, Wei Zhang, Huan Xie, Liwei Liu, Sujie Huang, Xiao Li, Zhengzheng Zhang, Yuyang Liu, Bangzhi Zhang, Jingjing Song, Rui Wang

CCL 2018 Vol. 29 (07): 1163-1166 DOI:10.1016/j.cclet.2018.04.011

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Conformational flexibility induced by proline and aminocaproic acid can increase anticancer activity and antimicrobial activity of dimeric antimicrobial peptides with reduced hemolytic activity. This study will contribute to the design of efficient antimicrobial peptides.

Stapled SC34EK fusion inhibitors with high potency against HIV-1 and improved protease resistance

Ye Guo, Lili Fu, Xiaowen Fan, Xuanling Shi

CCL 2018 Vol. 29 (07): 1167-1170 DOI:10.1016/j.cclet.2018.03.024

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A single all-hydrocarbon staple introduction in SC34EK can afford a potent HIV inhibitor with high protease resistance for ADIS treatment.

In vitro and in vivo evaluation of improved EGFR targeting peptide-conjugated phthalocyanine photosensitizers for tumor photodynamic therapy

Qingle Chen, Yanhong Ma, Jisi Zhao, Mei Zhao, Wenjing Li, Qian Liu, Li Xiong, Wenjie Wu, Zhangyong Hong

CCL 2018 Vol. 29 (07): 1171-1178 DOI:10.1016/j.cclet.2018.04.025

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A serial of peptide-conjugated zinc phthalocyanines with finely tuned structure modification were prepared and one optimized conjugate showed improved targeting towards tumors and abolished inoculated tumors with only a single PDT treatment in a subcutaneous xenograft tumor model, making this approach a promising therapeutic agent for the treatment of cancer.