Article
Chemistry, Organic
Nathalie Ollivier, Eliott Roy, Vangelis Agouridas, Vincent Diemer, Oleg Melnyk
Summary: 4-Mercaptophenylacetic acid (MPAA) is a commonly used catalyst for native chemical ligation (NCL), but it requires a large excess for practical rates (up to 50-100 equivalents). In this study, we found that the catalytic potency of MPAA can be enhanced by introducing a stretch of arginines in the departing thiol of the thioester. This electrostatically assisted NCL reaction allows for rapid synthesis using substoichiometric concentrations of MPAA, which is advantageous for practical applications.
Article
Chemistry, Analytical
Siyun Chen, Di Wu, Carol Robinson, Weston B. Struwe
Summary: The heterogeneity of glycoproteins poses a major challenge in structural biology, but the combination of native mass spectrometry with glycan exoglycosidase sequencing offers remarkable details of glycoprotein structures. This approach significantly improves the ability to characterize protein glycosylation and address the need for structural biology, opening up new avenues for understanding glycoprotein function.
ANALYTICAL CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Mohadeseh Dastpeyman, John A. Karas, Azin Amin, Bradley J. Turner, Fazel Shabanpoor
Summary: Cell penetrating peptides (CPPs) are efficient vectors for intracellular delivery of biologically active agents like therapeutic antisense oligonucleotides (ASOs). Conjugating ASOs to CPPs through native chemical ligation (NCL) significantly improves their cellular permeability and therapeutic efficacy. This study demonstrates that chemo-selective NCL is a superior strategy for synthesizing bi-/trifunctional CPP-ASO conjugates with high efficiency.
FRONTIERS IN CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Sebastian Trunschke, Emanuele Piemontese, Olaf Fuchs, Skander Abboud, Oliver Seitz
Summary: By introducing new ligation auxiliaries, this study expands the applicability of native chemical ligation and investigates the role of the pyridine-ring nitrogen in the auxiliaries. The study successfully synthesizes peptides with special structures, demonstrating that the new auxiliary has increased stability and wide application potential.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Evelyn M. Molloy, Maria Dell, Veit G. Haensch, Kyle L. Dunbar, Romy Feldmann, Ansgar Oberheide, Lydia Seyfarth, Jana Kumpfmueller, Therese Horch, Hans-Dieter Arndt, Christian Hertweck
Summary: This study reports the discovery of a genuine chemical mediator, homodetic cyclopeptide (cAIP), that controls endospore formation in clostridia, and reveals a widespread feature of clostridial AIP biosynthesis, namely the novel enzyme-primed, intramolecular native chemical ligation (NCL).
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Dipankar Chaudhuri, Rajasekaran Ganesan, Alicia Vogelaar, Mansour A. Dughbaj, Paul M. Beringer, Julio A. Camarero
Summary: A new epimerization-free approach for the Fmoc-based synthesis of murepavadin using intramolecular native chemical ligation and desulfurization reaction has been developed, resulting in a high yield of bioactive murepavadin in two steps. The synthetic peptide antibiotic showed potent activity against different clinical isolates of P. aeruginosa. This approach can be easily adapted for the production of murepavadin analogues and other backbone-cyclized peptides.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Shaomin Lin, Zeyuan Mo, Peng Wang, Chunmao He
Summary: In order to meet the demand for peptide salicylaldehyde esters, we developed a new method for the preparation of these esters from peptide hydrazides through nitrite oxidation and phenolysis. This method is simple and suitable for both synthetic peptides and expressed proteins, facilitating peptide synthesis and the combined application of NCL and STL.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Analytical
Steffen Lippold, Steffen Lippold, Raashina Thavarajah, Raashina Thavarajah, Dietmar Reusch, Dietmar Reusch, Manfred Wuhrer, Manfred Wuhrer, Simone Nicolardi, Simone Nicolardi
Summary: Recombinant human erythropoietin (EPO) is a complex therapeutic glycoprotein with several glycosylation sites, and the analysis of EPO glycosylation is crucial for its safety and efficacy. Various mass spectrometry methods are used to study EPO glycosylation, with ESI MS providing comprehensive insights into intact EPO glycoform heterogeneity.
ANALYTICA CHIMICA ACTA
(2021)
Article
Chemistry, Multidisciplinary
Luisa Maria Gatzemeier, Franc Meyer, Ulf Diederichsen, Tiago Fleming Outeiro
Summary: Alpha-Synuclein is a protein involved in neurodegenerative disorders that accumulate in brain protein inclusions. We have developed a chemical synthesis method for Alpha-Synuclein, allowing the synthesis of protein variants for further investigation of its structure and aggregation behavior.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Olaf Fuchs, Sebastian Trunschke, Hendrik Hanebrink, Marc Reimann, Oliver Seitz
Summary: This study introduces a new auxiliary, MPyE, designed to catalyze ligation reactions in chemical protein synthesis. The MPyE auxiliary proves to be effective in providing useful rates even for junctions containing proline or a beta-branched amino acid.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
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
Biochemistry & Molecular Biology
Anna Kataki-Anastasakou, Selena Hernandez, Ellen M. Sletten
Summary: The widespread adoption of the bioorthogonal chemical reporter strategy has revolutionized chemical biology, but its translation to living mammals has been challenging. This study introduces a novel bioorthogonal complexation approach, leveraging intermolecular interactions instead of new bioorthogonal reactions, to efficiently label cell surfaces and implement in the chemical reporter strategy.
ACS CHEMICAL BIOLOGY
(2021)
Article
Chemistry, Organic
Jie Zhao, Jiazhi Liu, Xinliang Liu, Farong Ye, Siyao Wang, Ping Wang
Summary: IL-1 alpha was semi-synthesized using expressed threonine ligation and native chemical ligation-desulfurization. This method can be applied to the synthesis of other Cys-free glycoproteins.
TETRAHEDRON LETTERS
(2022)
Article
Chemistry, Organic
Avijit K. Adak, Yung-Yu Su, Wei-Hao Wang, Chin-Lan Lin, Hao Gu, Yi-Chen Huang, Zhe-Jie Zhang, Chai-Lin Kao, Chun-Cheng Lin
Summary: Photoactivatable ligation auxiliaries simplify protein assembly by cleaving the auxiliary after ligation through photolysis. This study introduces an easy-to-attach TmNpE-auxiliary at the internal side-chain of N-terminal peptide fragments, enabling long-range ligation and photolytic removal in an aqueous buffer. The method's versatility is demonstrated by synthesizing a hPD-L1 peptide inhibitor. The TmNpE group offers easy introduction, compatibility with peptide ligation reactions, and mild cleavage conditions.
Article
Chemistry, Multidisciplinary
Daisuke Matsui, Yoshiyuki Hirata, Akihisa Iwakawa, Yosuke Toyotake, Mamoru Wakayama, Yasuhisa Asano
Summary: The formation of amide bonds through the ligation of N-hydroxylamine and alpha-keto acid, catalyzed by porcine kidney D-amino acid oxidase, achieved high yields of amides. This method offers a practical approach for the synthesis of various amide compounds.
Article
Chemistry, Organic
Yuta Maki, Takanori Mima, Ryo Okamoto, Masayuki Izumi, Yasuhiro Kajihara
JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Multidisciplinary
Masayuki Izumi, Rie Kuruma, Ryo Okamoto, Akira Seko, Yukishige Ito, Yasuhiro Kajihara
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2017)
Article
Chemistry, Multidisciplinary
Tatsuto Kiuchi, Masayuki Izumi, Yuki Mukogawa, Arisa Shimada, Ryo Okamoto, Akira Seko, Masafumi Sakono, Yoichi Takeda, Yukishige Ito, Yasuhiro Kajihara
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2018)
Article
Biochemistry & Molecular Biology
Ryo Okamoto, Takuya Haraguchi, Kota Nomura, Yuta Maki, Masayuki Izumi, Yasuhiro Kajihara
Article
Chemistry, Multidisciplinary
Ryo Okamoto, Emiko Ono, Masayuki Izumi, Yasuhiro Kajihara
FRONTIERS IN CHEMISTRY
(2019)
Article
Chemistry, Multidisciplinary
Chaitra Chandrashekar, Ryo Okamoto, Masayuki Izumi, Yasuhiro Kajihara
CHEMISTRY-A EUROPEAN JOURNAL
(2019)
Article
Chemistry, Organic
Yuta Maki, Kota Nomura, Ryo Okamoto, Masayuki Izumi, Yasuhisa Mizutani, Yasuhiro Kajihara
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Masayuki Izumi, Hiroyuki Araki, Mamiko Tominaga, Ryo Okamoto, Yasuhiro Kajihara
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Multidisciplinary
Yuta Maki, Ryo Okamoto, Masayuki Izumi, Yasuhiro Kajihara
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2020)
Article
Biochemistry & Molecular Biology
Naoki Tsutsumi, Akitaka Ito, Azumi Ishigamori, Masato Ikeda, Masayuki Izumi, Rika Ochi
Summary: In this study, a novel bola-amphiphilic glycosylated lipopeptide-type supramolecular hydrogelator is presented, exhibiting reversible thermochromism and gel-sol transition. The investigation focused on the effects of different numbers of F residues on gelation ability and morphology of self-assembled nanostructures.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2021)
Article
Biochemistry & Molecular Biology
Yuta Maki, Yuiko Otani, Ryo Okamoto, Masayuki Izumi, Yasuhiro Kajihara
Summary: High-mannose type glycans play significant roles in the biosynthesis and quality control of glycoproteins. In this study, we isolated and confirmed the identical structures of M5-glycan and M6-glycan to human-type glycans, suggesting their potential use in glycan analysis and the semisynthesis of glycoconjugates.
CARBOHYDRATE RESEARCH
(2022)
Article
Chemistry, Multidisciplinary
Naoki Tsutsumi, Akitaka Ito, Yosuke Niko, Yui Bando, Kiyonori Takahashi, Masato Ikeda, Kaori Yoneyama, Takayoshi Nakamura, Masayuki Izumi, Rika Ochi
Summary: In this study, we developed glycolipid-type amphiphiles with aggregation-induced emission (AIE) features and found that the design of molecular packing plays a crucial role in controlling the AIE properties.
Article
Chemistry, Physical
Ryoya Oosumi, Masato Ikeda, Akitaka Ito, Masayuki Izumi, Rika Ochi
Article
Chemistry, Multidisciplinary
Ryo Orii, Noriko Sakamoto, Daichi Fukami, Sakae Tsuda, Masayuki Izumi, Yasuhiro Kajihara, Ryo Okamoto
CHEMISTRY-A EUROPEAN JOURNAL
(2017)
Article
Chemistry, Multidisciplinary
Nguyen Minh Hien, Masayuki Izumi, Hajime Sato, Ryo Okamoto, Yasuhiro Kajihara
CHEMISTRY-A EUROPEAN JOURNAL
(2017)