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4. Solid-phase synthesis of fluorescent analogues of Park's nucleotide, lipid I and lipid II

Author

Katsuyama, Akira, Yakushiji, Fumika, and Ichikawa, Satoshi

Subjects
Fluorescent probe, Solid-phase synthesis, Peptidoglycan
Abstract

Solid-phase modular synthesis of fluorescent analogues of Park's nucleotide, lipid I and II, is described. The Fmoc protected lysine side chain of resin-bound intermediates were selectively modified by various fluorescent groups. This is the first example of solid-phase synthesis of these compounds. This synthetic strategy allows the preparation of various fluorescent probes for investigating the mechanisms of bacterial cell-wall biosynthesis. (C) 2021 Published by Elsevier Ltd.

Published
2021

13. Negamycin Analogue with Readthrough-Promoting Activity as a Potential Drug Candidate for Duchenne Muscular Dystrophy

Author

Taguchi, Akihiro, primary, Nishiguchi, Shigenobu, additional, Shiozuka, Masataka, additional, Nomoto, Takao, additional, Ina, Mayuko, additional, Nojima, Shouta, additional, Matsuda, Ryoichi, additional, Nonomura, Yoshiaki, additional, Kiso, Yoshiaki, additional, Yamazaki, Yuri, additional, Yakushiji, Fumika, additional, and Hayashi, Yoshio, additional

Published
2012
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15. Total Synthesis of Plusbacin A 3 and Its Dideoxy Derivative Using a Solvent-Dependent Diastereodivergent Joullié-Ugi Three-Component Reaction.

Author

Katsuyama A, Yakushiji F, and Ichikawa S

Subjects
Cyanides chemistry, Esterification, Lactones chemistry, Molecular Structure, Propanols chemistry, Stereoisomerism, Depsipeptides chemical synthesis, Depsipeptides chemistry, Solvents chemistry
Abstract

Full details of our synthetic studies toward plusbacin A 3 (1), which is a depsipeptide with antibacterial activity, and its dideoxy derivative are described. To establish an efficient synthetic route of 1, a solvent-dependent diastereodivergent Joullié-Ugi three-component reaction (JU-3CR) was used to construct trans-Pro(3-OH) in a small number of steps. Two strategies were investigated toward the total synthesis. In the first synthetic strategy, the key steps were the trans-selective JU-3CR and a macrolactonization at the final stage of the synthesis. The JU-3CR using alkyl isocyanides in 1,1,1,3,3,3-hexafluoroisopropanol provided the trans products, and the coupling of the fragments to prepare the macrocyclization precursor proceeded smoothly. However, attempts toward the macrolactonization did not provide the desired product. Then, the second strategy that included esterification in an initial stage was investigated. Methods for constructing trans-Pro(3-OH) were examined using a convertible isocyanide, which could be converted to a carboxylic acid required for the following amidation. Ester bond formation was achieved through an intermolecular coupling using a hydroxyl-Asp derivative and the corresponding alcohol, and the amidation afforded a linear depsipeptide. The macrolactamization of the linear peptide gave the cyclic depsipeptide, and then the global deprotection accomplished the total synthesis of 1 and its dideoxy derivative.

Published
2018
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16. Solid-Phase Modular Synthesis of Park Nucleotide and Lipids I and II Analogues.

Author

Katsuyama A, Sato K, Yakushiji F, Matsumaru T, and Ichikawa S

Subjects
Molecular Conformation, Monosaccharides chemistry, Nucleotides chemistry, Oligopeptides chemistry, Uridine Diphosphate N-Acetylmuramic Acid chemical synthesis, Uridine Diphosphate N-Acetylmuramic Acid chemistry, Monosaccharides chemical synthesis, Nucleotides chemical synthesis, Oligopeptides chemical synthesis, Solid-Phase Synthesis Techniques, Uridine Diphosphate N-Acetylmuramic Acid analogs & derivatives
Abstract

A solid-phase synthesis of Park nucleotide as well as lipids I and II analogues, which is applicable to the synthesis of a range of analogues, is described in this work. This technique allows highly functionalized macromolecules to be modularly labeled. Multiple steps are used in a short time (4 d) with a single purification step to synthesize the molecules by solid-phase synthesis.

Published
2018
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