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Related Concept Videos

Peptidoglycan Synthesis01:28

Peptidoglycan Synthesis

Structure of PeptidoglycanPeptidoglycan is a vital structural component of the bacterial cell wall, providing mechanical strength and shape to the cell. It consists of repeating units of two sugars—N-acetylglucosamine (NAG) and N-acetylmuramic acid (NAM)—linked by β-1,4 glycosidic bonds. These sugar chains are cross-linked by short peptide chains, forming a mesh-like polymer that surrounds the bacterial plasma membrane.Cytoplasmic Phase – Precursor SynthesisPeptidoglycan biosynthesis begins in...
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Related Experiment Video

Updated: Jun 18, 2026

Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities
09:10

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Published on: May 27, 2015

Synthesis of glycocinnasperimicin D.

Taihei Nishiyama1, Yoshifumi Kusumoto, Ken Okumura

  • 1School of Bioagricultural Sciences, Nagoya University, Chikusa, Nagoya 464-8601, Japan.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|November 26, 2009
PubMed
Summary

Scientists achieved the first total synthesis of the amino sugar antibiotic glycocinnasperimicin D. This involved a convergent strategy, key coupling reactions, and the development of novel synthetic methods for its construction.

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Published on: February 7, 2019

Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Synthetic Chemistry

Background:

  • Amino sugar antibiotics are crucial in combating bacterial infections.
  • Glycoconjugates play vital roles in biological processes.
  • The total synthesis of complex natural products like glycocinnasperimicin D presents significant chemical challenges.

Purpose of the Study:

  • To achieve the first total synthesis of the amino sugar antibiotic glycocinnasperimicin D.
  • To develop efficient synthetic strategies for constructing complex glycosylated molecules.
  • To overcome synthetic roadblocks in the preparation of glycocinnasperimicin D.

Main Methods:

  • Convergent, three-component coupling strategy.
  • Heck-Mizoroki reaction for core structure assembly.
  • Synthesis of urea glycoside via glycosyl isocyanate intermediate.

Main Results:

  • Successful total synthesis of glycocinnasperimicin D (1).
  • Development of an alpha-selective phenyl glycosylation process.
  • Establishment of a selective acetonide deprotection method.

Conclusions:

  • The developed synthetic route provides access to glycocinnasperimicin D.
  • The novel synthetic methodologies can be applied to other complex glycosylated natural products.
  • This synthesis opens avenues for further biological evaluation and drug development.