Article
Biotechnology & Applied Microbiology
Angel Espinoza-Gonzalez, Carmen Hernandez-Valencia, Luis Cedeno-Caero, Roberto Sanchez-Sanchez, Carmina Montiel, Miquel Gimeno
Summary: Subtilisin Carlsberg, an alkaline protease from Bacillus licheniformis, can catalyze the synthesis of high molecular weight cationic alpha-poly-L-lysine and amphiphilic poly(alpha-L-lysine-co-L-phenylalanine) in organic solvent. The reaction is conducted in hydrophobic non-toxic 1,1,1,2-tetrafluoroethane solvent, and the low water environment limits hydrolysis of the peptide chains. The organic compressed fluid used in the reaction has low-pressure requirements and evaporates completely after the reaction, leaving no solvent residues. The resulting polypeptides show no cytotoxicity in human cells.
BIOPROCESS AND BIOSYSTEMS ENGINEERING
(2023)
Article
Chemistry, Multidisciplinary
Maxim M. Veselov, Igor Uporov, Maria Efremova, Irina M. Le-Deygen, Andrey N. Prusov, Igor Shchetinin, Alexander G. Savchenko, Yuri Golovin, Alexander Kabanov, Natalia L. Klyachko
Summary: The conjugation of enzymes to magnetic nanoparticles can lead to changes in their catalytic activity under nonheating low-frequency magnetic fields. In this study, alpha-chymotrypsin (CT) conjugated to gold-coated iron oxide nanoparticles was investigated. The results showed that the stretching force applied to the CT globule by the amino or carboxylic groups attached to the nanoparticles caused shrinkage of the substrate-binding site, but had little effect on the catalytic triad. The magnetic field altered the Michaelis-Menten constant, but not the apparent catalytic constant. Additionally, the secondary structure of CT was affected, with a loss of alpha-helices and an increase in random structures. However, both the catalytic activity and the protein structure of the conjugates were restored after 3 hours of field exposure. These remotely actuated systems have potential applications in advanced manufacturing, nanomedicine, and other areas.
Article
Chemistry, Multidisciplinary
Kazuki Sato, Tomohiro Umeno, Atsushi Ueda, Takuma Kato, Mitsunobu Doi, Masakazu Tanaka
Summary: The N-terminal thiourea-modified l-Leu-based peptide catalyst demonstrated high enantioselectivity in the 1,4-addition reaction, requiring only a small amount for efficient reaction under different substrate and donor conditions.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Alagesan Muthuvinothini, Selvaraj Stella
Summary: In this study, a highly chemoselective method for the coupling of carbodiimides with primary amines to synthesize guanidines was achieved using L-cysteine capped zinc nanoparticles as a catalyst. The efficiency of the catalyst was demonstrated through recyclability and reusability studies, with surface characterization before and after repetitive usage confirming the stability of the catalyst.
SYNTHETIC COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Naoki Kamo, Tomoya Kujirai, Hitoshi Kurumizaka, Hiroshi Murakami, Gosuke Hayashi, Akimitsu Okamoto
Summary: The utilization of an air-tolerant organoruthenium catalyst has enabled a more efficient and rapid synthesis of medium-sized proteins with site-specific PTMs, as well as facilitating rapid deprotection of proteins even in the presence of excess thiol moieties. This new ruthenium chemistry approach paves the way for the preparation of a variety of biologically and medically significant proteins containing PTMs and non-natural amino acids.
Article
Chemistry, Multidisciplinary
Madhav L. Ghimire, Bobby D. Cox, Cole A. Winn, Thomas W. Rockett, Nicholas P. Schifano, Hannah M. Slagle, Frank Gonzalez, Massimo F. Bertino, Gregory A. Caputo, Joseph E. Reiner
Summary: Recent research has shown that ligand-induced structure fluctuations of gold nanoclusters can be monitored using resistive-pulse nanopore sensing. The fluctuations can be used to identify the attaching peptide, either through the magnitude of current jumps or the onset of high-frequency current fluctuations. The presence of a cysteine residue in the peptide is required for the attachment process, suggesting that this method could be used for selective detection of cysteine-containing peptides. The study also demonstrates the ability to identify multiple cysteine-containing peptides in a mixture.
Article
Biotechnology & Applied Microbiology
Taku Mizutani, Ryotaro Hara, Takayuki Iihoshi, Shoko Kozono, Michiki Takeuchi, Makoto Hibi, Satomi Takahashi, Makoto Ueda, Jun Ogawa
Summary: This study found that E. coli has the ability to synthesize S-allyl-L-cysteine (SAC) through the enzyme tryptophanase (TnaA). TnaA also showed the ability to synthesize a wide range of S-substituted cysteines with various chains or rings. These findings have important implications for the development of new processes for synthesizing valuable S-substituted cysteine derivatives.
JOURNAL OF BIOSCIENCE AND BIOENGINEERING
(2022)
Article
Chemistry, Multidisciplinary
Wenxiu Lv, Maosheng Li, Youhua Tao
Summary: Poly((L)-lysine) (PLL) is a water-soluble cationic biopolymer that can be modified via reactions between the side amine groups and functional moieties. The synthesis of PLL-based polypeptides through ring-opening polymerization has been challenging due to the difficulty in obtaining high-purity N-carboxyanhydrides (NCAs). This study achieves a scale-up synthesis of (L)-Cbz-LysNCA monomer and its polymers, providing a foundation for industrial preparation and expanding the applications of PLL-based polypeptides.
CHINESE JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Medicinal
Xiaoxin Chen, Peng Li, Jianzhou Huang, Yaxun Yang, Haoyu Zhang, Zheng Wang, Zhenzhen Zhu, Jingjing Wang, Jianchen Zhang, Kevin Chen, Haiying He, Chaofeng Long, Shuhui Chen
Summary: The outbreak of SARS-CoV-2 has caused a global health and economic crisis. The use of Paxlovid requires specialized assessment of the multiple drug-drug interaction risk associated with ritonavir. We report a multiple-round SAR study that introduces a novel bicyclic [3.3.0]proline peptidyl a-ketoamide compound 4a, which exhibits excellent antiviral activities and pharmacokinetic properties. In vivo experiments using an HCoV-OC43 neonatal mice model demonstrate the good efficacy of compound 4a. Based on these findings, further SAR optimization is warranted to develop compounds with improved pharmacokinetic properties and ultimately achieve single agent efficacy in humans.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2023)
Article
Chemistry, Organic
Yi Xiao, Yangyang Jiang, Chao Xu, Pratanphorn Nakliang, Sanghee Yoon, Sun Choi, Yian Guo, Tao Ye
Summary: The stereocontrolled total synthesis of the antitumor natural product thioamycolamide A has been achieved in 14 steps with an overall yield of 19.1%. The key aspect of our approach is the preparation of the beta-alkylthio amide subunit through an auxiliary-controlled, diastereoselective sulfa-Michael addition.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Polymer Science
Jianwei Guo, Xiao Liu, Ming Liu, Miaomiao Han, Yadong Liu, Shengxiang Ji
Summary: In this study, poly(L-lactic acid) (PLLA) was plasticized with poly(ethylene glycol) (PEG) to improve its brittleness, and the effects of PEG molecular weight and content on the properties of PLLA/PEG blends were systematically studied. The competition between phase separation and PLLA crystallization was found to determine the final structures and physical properties of PLLA/PEG blends, with different PEG contents and molecular weights influencing the crystallization form and mechanical properties of the blends.
Article
Chemistry, Multidisciplinary
Isaac Benavides, Eric D. Raftery, Alexandra G. Bell, Declan Evans, Wendell A. Scott, K. N. Houk, Timothy J. Deming
Summary: A new soluble poly(S-alkyl-L-cysteine) precursor was designed for the successful preparation of long-chain poly(dehydroalanine) and the incorporation of dehydroalanine residues and A(DH) segments into copolypeptides. A(DH) was found to adopt a unique hybrid coil structure and possess inherent blue fluorescence suitable for imaging applications. Its reactive electrophilic groups allow for efficient modification under mild conditions, making it a unique component for self-assembled biomaterials.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Yaodong Wang, Yudan Wang, Lijia Liu, Kexiao Sang, Chunhong Zhang, Toshifumi Satoh
Summary: Metal-free catalysts have emerged as an important research focus in catalysis due to the growing concern over heavy metal pollution. In this study, a heterogeneous catalyst, l-Pro-l-Pro-l-Phe-l-Phe-OMe, was synthesized by connecting an aromatic amino acid dipeptide (l-Phe-l-Phe-OMe) with a proline dipeptide (l-Pro-l-Pro) through solid phase synthesis. The catalyst's structure was characterized using SEM, XRD, NMR, and FTIR spectroscopy, with X-ray diffractometry revealing a rod crystal structure. Furthermore, l-Pro-l-Pro-l-Phe-l-Phe-OMe exhibited superior catalytic activity compared to a homogeneous small molecule catalyst (high enantioselectivity, ee > 97%) in heterogeneous asymmetric aldol reactions and demonstrated good recyclability.
REACTION CHEMISTRY & ENGINEERING
(2023)
Article
Plant Sciences
Jiyoon Park, Jiseong Kim, Sunghoon Hwang, Daehyun Oh, Young Eun Du, Sang-Jip Nam, Hyeung-geun Park, Min Jae Lee, Dong-Chan Oh
Summary: New sulfur-bearing natural products, sadopeptins A and B, were discovered from Streptomyces sp. YNK18 through a targeted search using the isotopic signature of sulfur. The compounds were determined to be new cyclic heptapeptides with specific functional groups through NMR spectroscopy and other analyses. The findings also revealed the presence of a biosynthetic gene cluster and proposed a potential biosynthetic pathway. The sadopeptins showed proteasome-inhibitory activity without affecting cellular autophagic flux.
JOURNAL OF NATURAL PRODUCTS
(2023)
Article
Biochemistry & Molecular Biology
Takuya Matsumoto, Ruri Kitayama, Ryosuke Yamada, Hiroyasu Ogino
Summary: Some amino acids have low aqueous solubility, but this can be improved by dipeptides; Gly-Tyr has high aqueous solubility and can be rapidly degraded in the human body; The PST-01 protease from Pseudomonas aeruginosa PST-01 is stable in the presence of organic solvents and was utilized in the efficient synthetic method of a Gly-Tyr precursor.
PROCESS BIOCHEMISTRY
(2021)
Article
Biotechnology & Applied Microbiology
Jun Mitsuhashi, Tsutomu Nakayama, Asako Narai-Kanayama
ENZYME AND MICROBIAL TECHNOLOGY
(2015)
Article
Biochemistry & Molecular Biology
Asako Narai-Kanayama, Kosuke Saruwatari, Natsumi Mori, Tsutomu Nakayama
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY
(2018)
Article
Biochemistry & Molecular Biology
Asako Narai-Kanayama, Hiroyuki Koshino, Keiichi Aso
BIOCHIMICA ET BIOPHYSICA ACTA-GENERAL SUBJECTS
(2008)
Article
Biotechnology & Applied Microbiology
Asako Narai-Kanayama, Yuhei Kawamura, Masumi Hosono, Keiichi Aso
ENZYME AND MICROBIAL TECHNOLOGY
(2009)
Article
Biotechnology & Applied Microbiology
Asako Narai-Kanayama, Keiichi Aso
ENZYME AND MICROBIAL TECHNOLOGY
(2009)
Article
Food Science & Technology
Shunsuke Inoguchi, Yuji Ohashi, Asako Narai-Kanayama, Keiichi Aso, Takenori Nakagaki, Tomohiko Fujisawa
INTERNATIONAL JOURNAL OF FOOD SCIENCES AND NUTRITION
(2012)
Article
Biotechnology & Applied Microbiology
Asako Narai-Kanayama, Yasuhiro Shikata, Masumi Hosono, Keiichi Aso
JOURNAL OF BIOTECHNOLOGY
(2010)
Article
Food Science & Technology
Asako Narai-Kanayama, Norio Tokita, Atsuko Funayama, Keiichi Aso
JOURNAL OF THE JAPANESE SOCIETY FOR FOOD SCIENCE AND TECHNOLOGY-NIPPON SHOKUHIN KAGAKU KOGAKU KAISHI
(2013)
Article
Agriculture, Multidisciplinary
Asako Narai-Kanayama, Yoshinori Uekusa, Fumiyuki Kiuchi, Tsutomu Nakayama
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2018)
Article
Biochemistry & Molecular Biology
Asako Narai-Kanayama, Yuuka Uchida, Aya Kawashima, Tsutomu Nakayama
PROCESS BIOCHEMISTRY
(2019)
Article
Biochemistry & Molecular Biology
Fumiyuki Kobayashi, Risa Nakajima, Asako Narai-Kanayama, Sachiko Odake
PROCESS BIOCHEMISTRY
(2020)
Article
Chemistry, Applied
Asako Narai-Kanayama, Kazuhiro Chiku, Hiroshi Ono, Takamitsu Momoi, Miho Hiwatashi-Kanno, Akiko Kobayashi, Hiroko Matsuda, Mitsuru Yoshida, Tsutomu Nakayama
Summary: Theaflavin, the polyphenol responsible for the orange color and bioactivities of black tea, can undergo autoxidation to change its color to brown under neutral and mild alkaline conditions. The presence of thiol compounds such as cysteine, glutathione, or N-acetyl cysteine can inhibit the browning of theaflavin solution and lead to a decrease in the concentrations of both theaflavin and thiol group over time. LC-MS analysis revealed the formation of novel adducts of thiol compounds. The chemical structures of theaflavin-cysteine and theaflavin-glutathione adducts were determined using NMR, showing the addition of a new cyclic structure to the theaflavin-cysteine adduct.
Article
Food Science & Technology
Asako Narai-Kanayama, Shin-ichi Yokosaka, Yuji Seo, Kouji Mikami, Takayuki Yoshino, Hiroko Matsuda
Summary: This study found that raw spinach leaves contain 0.4-1.5 mg/100 g of phytol. The phytol content in smoothies made from spinach leaves can be increased through enzymatic reactions. These findings are useful for controlling the phytol content in smoothies.
JOURNAL OF FOOD SCIENCE
(2023)
Article
Microbiology
Tomohiko Fujisawa, Yuji Ohashi, Ryoichi Shin, Asako Narai-Kanayama, Takenori Nakagaki
BIOSCIENCE OF MICROBIOTA FOOD AND HEALTH
(2017)