Article
Chemistry, Organic
Yan-Ni Zhang, Qing-Hong Yin, Xiao-Lei Xie, Xiao-Cui Wan, Ge-Min Fang
Summary: A practical strategy for thioester ligation using peptide hydrazides as crypto-thioesters is introduced in this article. The N-terminal amino group of the intermediate thioester peptide reacts readily with its C-terminal thioester moiety via head-to-tail cyclisation in the convergent ligation strategy. Peptide hydrazide has not been used as a crypto-thioester in thioester ligation due to its reaction with thioesters in the presence of silver ion. However, the issue is addressed by selectively protecting the C-terminal acyl hydrazide using di-tert-butyl dicarbonate under acidic conditions. The robustness and easy operability of this strategy will enhance the utility of thioester ligation in chemical protein synthesis.
TETRAHEDRON LETTERS
(2023)
Article
Chemistry, Multidisciplinary
Hendrik Hessefort, Angelina Gross, Simone Seeleithner, Markus Hessefort, Tanja Kirsch, Lukas Perkams, Klaus Ole Bundgaard, Karen Gottwald, David Rau, Christopher Guenther Franz Graf, Elisabeth Rozanski, Sascha Weidler, Carlo Unverzagt
Summary: The in-vivo activity of EPO is carbohydrate-dependent, with the number of sialic acid residues regulating its circulatory half-life. A chemoenzymatic approach was developed for obtaining glycoforms of EPO with and without sialic acids. Synthetic EPOs showed biological recognition by forming 1:1 complexes with recombinant EPO receptor.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Hironobu Hojo, Toshiki Takei, Yuya Asahina, Nobuaki Okumura, Toshifumi Takao, Masatomo So, Isao Suetake, Takeshi Sato, Akihiro Kawamoto, Yoshio Hirabayashi
Summary: In this study, the essential protein Caveolin-1 for caveola formation was chemically synthesized and successfully inserted into the lipid bilayer to form a V-shaped structure. The solid-phase method was used to synthesize peptide segments, and O-acyl isopeptide structures were incorporated to improve solubility. After ligation by the thioester method and the introduction of palmitoyl groups, the obtained polypeptide was inserted into bicelles.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Siyao Wang, Qingqing Zhou, Yunxue Li, Bingcheng Wei, Xinliang Liu, Jie Zhao, Farong Ye, Zhongneng Zhou, Bei Ding, Ping Wang
Summary: Native chemical ligation (NCL) and expressed protein ligation (EPL) techniques provide efficient ways to assemble proteins with precise chemical features. This study introduces a quinoline-based photolabile protecting group (PPZQ) for cysteine, enabling various ligation strategies including NCL and EPL-desulfurization methods. The PPZQ group is compatible with radical desulfurization and shows great potential in protein caging/uncaging investigations.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Biochemistry & Molecular Biology
Maciej P. Paprocki, Jakob E. Rasmussen, Kasper K. Sorensen, Knud J. Jensen
Summary: The study introduces a new approach for the synthesis of peptide thioesters and hydrazides, utilizing the activation of the pGlu linker and a novel safety-catch linker. This method involves efficient amide-to-imide activation followed by nucleophilic displacement.
JOURNAL OF PEPTIDE SCIENCE
(2021)
Article
Chemistry, Multidisciplinary
Farong Ye, Jie Zhao, Peng Xu, Xinliang Liu, Jing Yu, Wei Shangguan, Jiazhi Liu, Xiaosheng Luo, Cheng Li, Tianlei Ying, Jing Wang, Biao Yu, Ping Wang
Summary: Investigating the role of carbohydrate domains in RBD glycoproteins is crucial for the development of neutralizing antibodies and vaccines against SARS-CoV-2, but the high heterogeneity of glycoforms may result in incomplete neutralization effects. This study presents an efficient and scalable strategy for preparing six glycosylated RBDs with defined structure glycoforms, providing insights into the structure-function relationships of carbohydrates.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Biochemistry & Molecular Biology
Florent Kerdraon, Gemma Bogard, Benoit Snella, Herve Drobecq, Muriel Pichavant, Vangelis Agouridas, Oleg Melnyk
Summary: Thiol-based catalysts are commonly used for chemical protein synthesis, but the development of selenol-based catalysts is still in its early stages. This study compared different selenols for their ability to promote thiol-thioester exchanges and demonstrated the successful total synthesis of a biologically active human chemotactic protein using a selected selenol compound.
Review
Chemistry, Multidisciplinary
Richard J. Spears, Cliona McMahon, Vijay Chudasama
Summary: The use of protecting groups for the cysteine thiol group has allowed for advancements in peptide and protein chemistry, enabling the synthesis of complex disulfide-rich peptides, protein semisynthesis, and labeling both in vitro and in vivo. Researchers have developed over 60 individual protecting groups for cysteine, showcasing their importance in peptide synthesis and protein science.
CHEMICAL SOCIETY REVIEWS
(2021)
Article
Chemistry, Multidisciplinary
Lucas Kambanis, Timothy S. Chisholm, Sameer S. Kulkarni, Richard J. Payne
Summary: This study introduces an iterative one-pot peptide ligation strategy that combines the rapid diselenide-selenoester ligation reaction with photodeselenisation chemistry, enabling the efficient synthesis of protein fragments in a short period of time. The use of a novel photolabile protecting group for selenocysteine side chains allows for mild, reagent-free deprotection using visible light, facilitating subsequent ligation reactions without the need for purification.
Article
Chemistry, Multidisciplinary
Tao Wang, Xiuxiu Cao, Yong Zheng, Chenchen Chen, Li Zhou, Demeng Sun, Gemin Fang, Changlin Tian
Summary: A practical strategy for the total stepwise solid-phase synthesis of peptide-oligonucleotide conjugates was developed using Boc/tBu protecting groups for specific amino acids. This strategy avoids depurination of the oligonucleotide caused by strong acid treatment and allows for easier availability of the necessary amino acids. The side reaction of deguanidination of the Arg residue can also be avoided with this protection strategy.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Xiao-Lei Xie, Jing-Ze Qi, Xiao-Cui Wan, Suo-De Zhang, Yan-Ni Zhang, Ge-Min Fang
Summary: We present a robust and practical method for chemical protein synthesis using an o-nitrobenzyl group as a temporary protective group. Through further investigation, we establish a reliable strategy for the quantitative photodeprotection of the o-nitrobenzyl group. This stable protective group is successfully applied in the chemical synthesis of a programmed death ligand 1 fragment, providing a practical approach for hydrazide-based native chemical ligation.
Article
Chemistry, Multidisciplinary
Sabrina Leichnitz, Komadhie C. Dissanayake, Arthur H. Winter, Peter H. Seeberger
Summary: Protective groups that can be selectively removed under mild conditions are important in carbohydrate chemistry. This study explores different BODIPY protecting groups for their usefulness in glycan synthesis. A BODIPY group with a boron difluoride unit is stable during glycosylations but can be cleaved with green light, as demonstrated by the assembly of a trisaccharide.
CHEMICAL COMMUNICATIONS
(2022)
Article
Multidisciplinary Sciences
Nathalie Ollivier, Magalie Senechal, Remi Desmet, Benoit Snella, Vangelis Agouridas, Oleg Melnyk
Summary: Phosphorylation is a mechanism used by cells to promote protein-biomolecule association. In this study, the authors demonstrate the effects of interactions between proteins equipped with positively charged arginines and peptides harboring negatively charged phosphoserines, enabling rate acceleration and chemical processes under dilute conditions.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Yassin M. Elbatrawi, Taylor Gerrein, Avraz Anwar, Kamlesh M. Makwana, David Degen, Richard H. Ebright, Juan R. Del Valle
Summary: We have achieved the total synthesis and configurational assignment of pargamicin A, a highly oxidized nonribosomal peptide that effectively inhibits the growth of drug-resistant bacteria. Our synthetic strategy involves late-stage piperazine ring formation and careful selection of condensation reagents to assemble the densely substituted hexapeptide backbone. This work facilitates the synthesis of pargamicin derivatives for structure-activity relationship studies and provides insights into accessing other piperazic acid-containing natural products with steric congestion.
Review
Chemistry, Multidisciplinary
Vangelis Agouridas, Nathalie Ollivier, Jerome Vicogne, Vincent Diemer, Oleg Melnyk
Summary: The last two decades have witnessed the rise in power of chemical protein synthesis, which now constitutes an established corpus of synthetic methods effectively complementing biological approaches. The emergence of chemoselective reactions enabling the formation of native peptide bonds between unprotected peptidic segments has contributed to this evolution. These native ligation reactions have fueled the production of homogeneous batches of large and highly decorated protein targets and have found successful applications in various fields such as chemical biology, medicinal chemistry, materials science, and nanotechnology research.
ACCOUNTS OF CHEMICAL RESEARCH
(2022)
Article
Chemistry, Multidisciplinary
Yuya Asahina, Shinobu Komiya, Ami Ohagi, Rina Fujimoto, Hiroko Tamagaki, Katsuhiro Nakagawa, Takashi Sato, Shizuo Akira, Toshifumi Takao, Akira Ishii, Yoshiaki Nakahara, Hironobu Hojo
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2015)
Article
Chemistry, Organic
Akihiro Taguchi, Kentarou Fukumoto, Yuya Asahina, Akihiro Kajiyama, Shunsuke Shimura, Keisuke Hamada, Kentaro Takayama, Fumika Yakushiji, Hironobu Hojo, Yoshio Hayashi
ORGANIC & BIOMOLECULAR CHEMISTRY
(2015)
Article
Biochemistry & Molecular Biology
Yuya Asahina
TRENDS IN GLYCOSCIENCE AND GLYCOTECHNOLOGY
(2015)
Article
Biochemistry & Molecular Biology
Yuya Asahina
TRENDS IN GLYCOSCIENCE AND GLYCOTECHNOLOGY
(2015)
Article
Chemistry, Multidisciplinary
Naoki Takeda, Toshiki Takei, Yuya Asahina, Hironobu Hojo
CHEMISTRY-A EUROPEAN JOURNAL
(2018)
Article
Biochemistry & Molecular Biology
Yuya Asahina, Rina Fujimoto, Akemi Suzuki, Hironobu Hojo
JOURNAL OF CARBOHYDRATE CHEMISTRY
(2015)
Article
Chemistry, Organic
Yuya Asahina, Hironobu Hojo
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Biochemistry & Molecular Biology
Mikito Nakano, Shinya Hanashima, Toshiaki Hara, Kazuya Kabayama, Yuya Asahina, Hironobu Hojo, Naoko Komura, Hiromune Ando, Thomas K. M. Nyholm, J. Peter Slotte, Michio Murata
Summary: GM3 in the plasma membranes suppresses cell growth by preventing the autophosphorylation of the epidermal growth factor receptor (EGFR). The lateral interaction between GM3 and the transmembrane segment of EGFR disturbs the formation of active EGFR dimers.
BIOCHIMICA ET BIOPHYSICA ACTA-BIOMEMBRANES
(2021)
Article
Chemistry, Organic
Shun Ito, Yuya Asahina, Hironobu Hojo
Summary: By employing a protecting group strategy, sialyl glycopeptides were synthesized successfully, providing easier access to sialyl glycoamino acids.
Article
Chemistry, Multidisciplinary
Yuya Asahina, Tatsuya Ando, Hironobu Hojo
Summary: This article presents a combination of protecting groups that enables the synthesis of glycopeptides containing acid-sensitive fucose. The relationship between the design of protecting groups for fucose alcohols and the acid stability of the fucosidic linkage is elucidated. The study found that a combination of 4-methylbenzyl and levulinoyl groups offers optimal protection of the fucosidic bond, allowing for the practical synthesis of glycopeptides containing fucose.
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
(2022)
Proceedings Paper
Green & Sustainable Science & Technology
Yuka Nimura, Kazuya Kabayama, Yuya Asahina, Shinya Hanashima, Hironobu Hojo, Michio Murata, Koichi Fukase
IRAGO CONFERENCE 2018: A 360-DEGREE OUTLOOK ON CRITICAL SCIENTIFIC AND TECHNOLOGICAL CHALLENGES FOR A SUSTAINABLE SOCIETY
(2019)
Article
Chemistry, Multidisciplinary
Kenta Arai, Toshiki Takei, Masaki Okumura, Satoshi Watanabe, Yuta Amagai, Yuya Asahina, Luis Moroder, Hironobu Hojo, Kenji Inaba, Michio Iwaoka
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2017)
Article
Chemistry, Medicinal
Pethaiah Gunasekaran, So-Rim Lee, Seung-Min Jeong, Jeong-Woo Kwon, Toshiki Takei, Yuya Asahina, Geul Bang, Seongnyeon Kim, Mija Ahn, Eun Kyung Ryu, Hak Nam Kim, Ki-Yub Nam, Song Yub Shin, Hironobu Hojo, Suk Namgoong, Nam-Hyung Kim, Jeong Kyu Bang
Article
Chemistry, Multidisciplinary
Yuya Asahina, Toru Kawakami, Hironobu Hojo
CHEMICAL COMMUNICATIONS
(2017)
