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Crossing Over

Crossing Over

Unlike mitosis, meiosis aims for genetic diversity in its creation of haploid gametes. Dividing germ cells first begin this process in prophase I, where each chromosome—replicated in S phase—is now composed of two sister chromatids (identical copies) joined centrally.
The homologous pairs of sister chromosomes—one from the maternal and one from the paternal genome—then begin to align alongside each other lengthwise, matching corresponding DNA positions in a process...

Crossing Over

Crossing Over

Crossing over is the exchange of genetic information between homologous chromosomes during prophase I of meiosis I. Genetic recombination gives rise to allelic diversity in the newly formed daughter cells. In humans, crossing over produces genetically distinct haploid egg and sperm cells that undergo fertilization to produce unique offspring. Before cell division starts, the germ cell’s chromosome(s) undergo duplication in the S phase of the cell cycle. As the cells enter prophase I,...

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In cross-sectional research, a researcher compares multiple segments of the population at the same time. If they were interested in people's dietary habits, the researcher might directly compare different groups of people by age. Instead of following a group of people for 20 years to see how their dietary habits changed from decade to decade, the researcher would study a group of 20-year-old individuals and compare them to a group of 30-year-old individuals and a group of 40-year-old...

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Alleles are different forms of the same gene. Humans and other diploid organisms inherit two alleles of every gene, one from each parent.

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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

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Published on: November 30, 2022

Stereoretentive C( sp³)-S Cross-Coupling.

Feng Zhu¹, Eric Miller¹, Shuo-Qing Zhang²

¹Department of Chemistry , University of Colorado , Boulder , Colorado 80309 , United States.

Journal of the American Chemical Society

|November 27, 2018

Summary

This study introduces a stereoretentive cross-coupling reaction for synthesizing thioglycosides and glycodiversifying peptides. The copper-promoted method offers controlled carbon-sulfur bond formation for late-stage applications.

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Published on: March 20, 2014

Area of Science:

Organic Chemistry
Carbohydrate Chemistry
Bioconjugation Chemistry

Background:

Efficient synthesis of thioglycosides and glycopeptides is crucial for drug discovery.
Late-stage functionalization of complex molecules remains a significant challenge in synthetic chemistry.

Purpose of the Study:

To develop a stereoretentive cross-coupling reaction for forming carbon-sulfur bonds.
To demonstrate the utility of this method in synthesizing thioglycosides and glycodiversifying peptides.

Main Methods:

Copper(I)-promoted cross-coupling of nucleophiles with disulfide and N-sulfenylsuccinimide donors.
Utilized carbohydrate substrates with common protecting groups and peptides with free hydroxyl/amide functionalities.
Employed competition experiments and computational DFT studies to elucidate reaction mechanisms.

Main Results:

Achieved stereoretentive synthesis of thioglycosides from alkyl/aryl thiols and thioglycosides.
Successfully performed glycodiversification of cysteine residues in peptides.
Identified a configurationally stable, short-lived organocopper intermediate resistant to epimerization.

Conclusions:

The developed glycosyl cross-coupling reaction is highly effective for late-stage glycodiversification and bioconjugation.
The method allows for controlled installation of aliphatic carbon-sulfur bonds under mild conditions.
The reaction's stereoretentive nature is attributed to a rapid and non-epimerizing reductive elimination step.