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ATP Energy Storage and Release01:31

ATP Energy Storage and Release

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ATP is a highly unstable molecule. Unless quickly used to perform work, ATP spontaneously dissociates into ADP and inorganic phosphate (Pi), and the free energy released during this process is lost as heat. The energy released by ATP hydrolysis is used to perform work inside the cell and depends on a strategy called energy coupling. Cells couple the exergonic reaction of ATP hydrolysis with endergonic reactions, allowing them to proceed.
One example of energy coupling using ATP involves a...
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Hydrolysis of ATP01:08

Hydrolysis of ATP

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The bonds of adenosine triphosphate (ATP) can be broken through the addition of water, releasing one or two phosphate groups in an exergonic process called hydrolysis. This reaction liberates the energy in the bonds for use in the cell—for instance, to synthesize proteins from amino acids.
If one phosphate group is removed, a molecule of ADP—adenosine diphosphate—remains, along with inorganic phosphate. ADP can be further hydrolyzed to AMP—adenosine...
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Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

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Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
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Glycolysis: Pay-off Phase01:25

Glycolysis: Pay-off Phase

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So far, glycolysis has cost the cell two ATP molecules and produced two small, three-carbon sugar molecules. These molecules will proceed through the second half of the pathway, and sufficient energy will be extracted to pay back the two ATP molecules used as an initial investment and produce a profit for the cell of two additional ATP molecules and two even higher-energy NADH molecules.
Step 1 - 5: Glycolysis Preparatory Phase
The first phase of glycolysis has 5 steps where the glucose is...
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Glycolysis: Preparatory Phase01:21

Glycolysis: Preparatory Phase

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In cellular metabolism (the complete breakdown of glucose to extract energy),  glycolysis is the first step. Glycolysis takes place in the cytoplasm of both prokaryotic and eukaryotic cells. Glucose enters heterotrophic cells in two ways. One method is through secondary active transport, where the transport takes place against the glucose concentration gradient. The other mechanism uses a group of integral proteins called GLUT proteins, also known as glucose transporter proteins. These...
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Acidity of 1-Alkynes02:42

Acidity of 1-Alkynes

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The acidic strength of hydrocarbons follows the order: Alkynes > Alkenes > Alkanes. The strength of an acid is commonly expressed in units of pKa — the lower the pKa, the stronger the acid. Among the hydrocarbons, terminal alkynes have lower pKa values and are, therefore, more acidic. For example, the pKa values for ethane, ethene, and acetylene are 51, 44, and 25, respectively, as shown here.
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Chemical Triphosphorylation of Oligonucleotides
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The Aryne Phosphate Reaction.

Thomas M Haas1, Stefan Wiesler1, Tobias Dürr-Mayer1

  • 1Institute of Organic Chemistry, Albert-Ludwigs University Freiburg, Albertstraße 21, 79102, Freiburg im Breisgau, Germany.

Angewandte Chemie (International Ed. in English)
|November 2, 2021
PubMed
Summary
This summary is machine-generated.

This study reveals phosphates can act as arynophiles, enabling new reactions to create functionalized phosphate molecules. This discovery facilitates the synthesis of complex nucleotide analogues and polyphosphates.

Keywords:
aryne chemistrymetaphosphatesoligophosphorylationphosphorylationpolyphosphates

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Area of Science:

  • Biochemistry
  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Condensed phosphates are vital in biochemistry and for applications like DNA sequencing.
  • Synthesizing non-natural phosphate analogues with extended chains requires novel reactivity.

Purpose of the Study:

  • To explore the reactivity of phosphates as arynophiles.
  • To develop new methods for phosphate functionalization and oligophosphorylation.
  • To enable the synthesis of diverse arylated phosphate compounds.

Main Methods:

  • Investigating the aryne phosphate reaction using Kobayashi-type o-silylaryltriflates.
  • Utilizing phosphates as nucleophiles in reactions with arynes.

Main Results:

  • Demonstrated that phosphates can act as arynophiles.
  • Developed a versatile aryne phosphate reaction for (oligo)phosphorylating arenes or arylating phosphates.
  • Synthesized a broad range of arylated products, including monophosphates, diphosphates, phosphodiesters, and polyphosphates.
  • Achieved efficient syntheses of nucleotide analogues and an eight-phosphate chain molecule in one flask.

Conclusions:

  • The aryne phosphate reaction offers a powerful and versatile route to arylated phosphate compounds.
  • This methodology significantly expands the toolkit for synthesizing complex phosphate structures.
  • The findings open new avenues for creating functionalized phosphates for biochemical and sequencing applications.