Hiroaki Sawamoto

ORCID: 0000-0003-2168-1207
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About
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Research Areas
  • Asymmetric Synthesis and Catalysis
  • Advanced biosensing and bioanalysis techniques
  • RNA Interference and Gene Delivery
  • DNA and Nucleic Acid Chemistry
  • Chemical Synthesis and Reactions
  • Sulfur-Based Synthesis Techniques
  • Coordination Chemistry and Organometallics
  • Carbohydrate Chemistry and Synthesis
  • Asymmetric Hydrogenation and Catalysis
  • Catalytic C–H Functionalization Methods
  • Chemical Synthesis and Analysis
  • Synthetic Organic Chemistry Methods
  • Chemical Reaction Mechanisms
  • Advanced Synthetic Organic Chemistry
  • Biotin and Related Studies
  • Click Chemistry and Applications
  • Traditional and Medicinal Uses of Annonaceae
  • Microbial Natural Products and Biosynthesis
  • MicroRNA in disease regulation
  • Axial and Atropisomeric Chirality Synthesis
  • RNA and protein synthesis mechanisms
  • Computational Drug Discovery Methods
  • Catalytic Cross-Coupling Reactions
  • Oxidative Organic Chemistry Reactions
  • Molecular spectroscopy and chirality

Clemson University
2023-2024

Mitsubishi Tanabe Pharma Corporation
2017-2023

Osaka University
2000-2005

Osaka University of Pharmaceutical Sciences
2004

β,β-Disubstituted chiral vinylic sulfoxides bearing functionalities have been synthesized via Cu-catalyzed conjugate addition of organozinc reagents to 1-alkynyl sulfoxides. Due the availability functionalized and high syn-selectivity reaction, both geometric β,β-disubstituted were selectively synthesized. Furthermore, derivatized into trisubstituted by trapping resulting α-sulfinyl carbanion with electrophiles. Highly diastereoselective THF THP ring formations accomplished means this...

10.1021/jo048747l article EN The Journal of Organic Chemistry 2004-11-01

[reaction: see text] A new synthetic method of chiral beta,beta-disubstituted vinylic sulfoxides bearing various functionalities has been developed by employing Cu-catalyzed conjugate addition an organozinc reagent to 1-alkynyl sulfoxide. Since the reaction proceeds with very high syn-selectivity, both geometric were stereoselectively synthesized changing combination sulfoxide and reagent.

10.1021/ol034289b article EN Organic Letters 2003-03-28

A transglycosylation reaction of 2'-amino-locked nucleic acid (LNA) from thymine (T) to other nucleobases adenine (A), guanine (G), and 5-methylcytosine (mC) has been developed. This proceeds in high yield with β-selectivity. The mild conditions enable the coexistence acid-labile protecting groups, including a 4,4'-dimethoxytrytyl (DMTr) group. 2'-Amino-LNAs bearing any nucleobase can now be easily synthesized.

10.1021/acs.orglett.8b00476 article EN Organic Letters 2018-03-12

The first example of an asymmetric intramolecular Michael addition reaction with use alpha-lithiated vinylic sulfoxide as a donor is reported. the to (Z)-enoates proceeds high diastereoselectivity give adducts (R)-configuration at beta-position ester in five-membered-ring formation. selectivity was reversed six-membered-ring resulting enolates were reacted alkyl halides or benzaldehyde diastereoselectivity.

10.1021/jo0492923 article EN The Journal of Organic Chemistry 2004-08-20

Facile synthesis of GuNA (guanidine-bridged nucleic acid) phosphoramidites bearing thymine, adenine, guanine, and 5-methylcytosine nucleobases a robust method for the preparation GuNA-modified oligonucleotides are described.

10.1039/d0ob01970d article EN Organic & Biomolecular Chemistry 2020-01-01

[figure: see text] The first example of an asymmetric intramolecular Michael addition reaction using alpha-lithiated vinylic sulfoxide as a donor is reported. the to (Z)-enoates proceeds with high diastereoselectivity give adducts having stereogenic center (R)-configuration at beta-position ester in cyclopentene ring formation. selectivity was reversed six-membered On other hand, corresponding (E)-enoates provided poor diastereoselectivity.

10.1021/ol006697a article EN Organic Letters 2000-12-05

Diastereoselective Ni(0)-catalyzed carbocyclization of enone to chiral vinylic sulfoxide has been accomplished, wherein two stereogenic centers were constructed simultaneously give cis- and trans-disubstituted cyclopentanes from (E)- (Z)-vinylic sulfoxides, respectively.

10.1039/b506375b article EN Chemical Communications 2005-01-01

Objective: The objective of this study was to provide experimental chemists with useful guidance for proper choice a reasonable cyclization precursor in macrolactonization which there are several options disconnection analysis. Keywords: Neoantimycin, Prunustatin A, Macrocyclization, DFT calculation, MD simulation.

10.2174/1570179413666160624105401 article EN Current Organic Synthesis 2017-02-07

2'-Amino-locked nucleic acid (ALNA), maintains excellent duplex stability, and the nitrogen at 2'-position is an attractive scaffold for functionalization. Herein, a facile efficient method synthesis of various 2'-N-acyl amino-LNA derivatives by direct acylation 2'-amino moiety contained in synthesized oligonucleotides its fundamental properties are described. The introduction acylated enhances potency molecules as therapeutic anti-microRNA oligonucleotides.

10.1039/d2ob01809h article EN Organic & Biomolecular Chemistry 2022-01-01

2'-Amino-locked nucleic acid has a functionalizable nitrogen atom at the 2'-position of its furanose ring that can provide desired properties to as scaffold. In this study, we synthesized novel acid, 2'-N-methanesulfonyl-2'-amino-locked (ALNA[Ms]) and conducted comparative studies on physical pharmacological ALNA[Ms] conventional acids, such 2'-methylamino-LNA (ALNA[Me]), which is classical 2'-amino-LNA derivative, also 2',4'-BNA/LNA (LNA). oligomers exhibited binding affinities for...

10.2139/ssrn.4363909 article EN 2023-01-01

Abstract ChemInform is a weekly Abstracting Service, delivering concise information at glance that was extracted from about 100 leading journals. To access of an article which published elsewhere, please select “Full Text” option. The original trackable via the “References”

10.1002/chin.200118032 article EN ChemInform 2001-05-01

Abstract ChemInform is a weekly Abstracting Service, delivering concise information at glance that was extracted from about 100 leading journals. To access of an article which published elsewhere, please select “Full Text” option. The original trackable via the “References”

10.1002/chin.200105035 article EN ChemInform 2001-01-30
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