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Related Concept Videos

Inhibitors of Gram-positive Cell Wall Synthesis01:23

Inhibitors of Gram-positive Cell Wall Synthesis

Bacterial cell walls are typically rigid structures composed mainly of peptidoglycan, a mesh-like polymer that provides mechanical strength and maintains cell shape. The synthesis of peptidoglycan is a crucial process in bacterial growth and serves as a primary target for many antibiotics.Mechanism of Action of Beta-Lactam AntibioticsBeta-lactam antibiotics, such as penicillin, inhibit peptidoglycan synthesis in actively growing cells. These antibiotics share a characteristic four-membered...
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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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Aminoglycosides constitute a highly potent class of bactericidal antibiotics that exert their antimicrobial effects by targeting the bacterial ribosome, specifically disrupting protein synthesis. These polycationic molecules consist of amino-modified sugars linked via glycosidic bonds to an aminocyclitol core such as 2-deoxystreptamine or streptamine. Their strong positive charges facilitate tight binding to the negatively charged phosphate backbone of ribosomal RNA (rRNA), primarily at the 16S...
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Protein glycosylation starts in the ER lumen and continues in the Golgi apparatus. Glycosyltransferases catalyze the addition of sugar molecules or glycosylation of proteins. Usually, these enzymes add sugars to the hydroxyl groups of selected serine or threonine residues to form O-linked glycans or the amino groups of asparagine residues to form N-linked glycans. Different positions on the same polypeptide chain can contain differently linked glycans.
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Penicillin, one of the earliest and most widely used antibiotics, is produced industrially by the filamentous fungus Penicillium chrysogenum. Large stirred-tank bioreactors ranging from tens to hundreds of thousands of liters maintain tightly controlled temperature, pH, and dissolved oxygen conditions to support fungal metabolism and maximize antibiotic yield. Penicillin is a secondary metabolite, synthesized primarily during the stationary growth phase, which requires a carefully managed...
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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
09:34

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

Published on: February 6, 2020

Difficulties encountered during glycopeptide syntheses.

J A Borgia1, N B Malkar, H U Abbasi

  • 1Department of Chemistry & Biochemistry, Florida Atlantic University, Boca Raton, FL 33431-0991, USA.

Journal of Biomolecular Techniques : JBT
|June 6, 2009
PubMed
Summary
This summary is machine-generated.

Solid-phase synthesis of glycopeptides has advanced, enabling incorporation of diverse carbohydrates. This review details challenges like unstable linkages and side reactions, offering solutions for efficient glycopeptide construction.

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Area of Science:

  • Carbohydrate Chemistry
  • Peptide Synthesis
  • Glycobiology

Background:

  • Solid-phase synthesis of glycopeptides has seen significant advancements.
  • Methods now allow incorporation of O- and N-linked glycosides and branched carbohydrates.
  • Construction of synthetic glycoproteins of modest size is achievable.

Purpose of the Study:

  • To review challenges in glycopeptide synthesis.
  • To provide solutions for problematic synthetic routes.
  • To highlight advancements in efficient glycopeptide construction.

Main Methods:

  • Overview of established solid-phase synthesis protocols.
  • Categorization of synthetic difficulties.
  • Presentation of specific examples and solutions.

Main Results:

  • Efficient incorporation of various glycosidic linkages (O- and N-linked, branched) is feasible.
  • Key challenges identified: unstable glycosidic linkages, difficult amino acid glycosylation, and side reactions.
  • Solutions are presented for overcoming these synthetic hurdles.

Conclusions:

  • Solid-phase glycopeptide synthesis is a mature field with established methodologies.
  • Understanding and addressing specific synthetic challenges is crucial for success.
  • Continued development offers pathways to complex synthetic glycoproteins.