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🥼organic chemistry review

Phosphite Triester

Written by the Fiveable Content Team • Last updated September 2025
Written by the Fiveable Content Team • Last updated September 2025

Definition

A phosphite triester is a type of organic compound that consists of a central phosphorus atom bonded to three organic substituents, typically alkyl or aryl groups. These compounds are important intermediates in the synthesis of DNA and other biomolecules.

5 Must Know Facts For Your Next Test

  1. Phosphite triesters are key intermediates in the synthesis of DNA, where they are used to form the phosphodiester backbone of the DNA molecule.
  2. The phosphite triester is first converted to a phosphoramidite, which then reacts with a nucleoside to form the DNA backbone.
  3. Phosphite triesters are highly reactive and must be handled under anhydrous conditions to prevent hydrolysis and decomposition.
  4. The use of phosphite triesters in DNA synthesis allows for the efficient and automated synthesis of DNA sequences, enabling the rapid production of genetic material.
  5. Phosphite triesters are also used in the synthesis of other biomolecules, such as RNA and modified nucleic acids, where they serve as key building blocks.

Review Questions

  • Explain the role of phosphite triesters in the synthesis of DNA.
    • Phosphite triesters are crucial intermediates in the automated synthesis of DNA. They are first converted to phosphoramidites, which then react with nucleosides to form the phosphodiester backbone of the DNA molecule. This allows for the efficient and rapid production of genetic material, as the phosphite triester-based approach enables the automated, step-by-step assembly of DNA sequences.
  • Describe the chemical properties and reactivity of phosphite triesters.
    • Phosphite triesters are highly reactive compounds that must be handled under anhydrous conditions to prevent hydrolysis and decomposition. The central phosphorus atom is bonded to three organic substituents, typically alkyl or aryl groups, which gives the compound its unique chemical properties. The reactivity of phosphite triesters is essential for their use in the synthesis of DNA and other biomolecules, as they can be readily converted to phosphoramidites and other reactive intermediates.
  • Analyze the broader applications of phosphite triesters beyond DNA synthesis.
    • While phosphite triesters are primarily known for their role in DNA synthesis, they have a wider range of applications in the synthesis of other biomolecules. These compounds can be used to synthesize RNA, as well as modified nucleic acids with altered properties. Additionally, phosphite triesters may be employed in the synthesis of other phosphorus-containing organic compounds, where their unique reactivity and ability to form stable intermediates make them valuable synthetic tools. The versatility of phosphite triesters extends beyond the field of DNA synthesis, highlighting their importance in various areas of organic and biomolecular chemistry.