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🥼organic chemistry review

2-cyanoethyl

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

Definition

The 2-cyanoethyl group is a functional group commonly used in the synthesis of DNA. It consists of a two-carbon chain with a cyano (nitrile) group attached to one of the carbon atoms, providing a protective group for the hydroxyl group during DNA synthesis.

5 Must Know Facts For Your Next Test

  1. The 2-cyanoethyl group is commonly used as a protecting group for the 5'-hydroxyl group of nucleosides during solid-phase DNA synthesis.
  2. The cyano group provides stability and prevents unwanted side reactions, allowing for the controlled addition of nucleotides to the growing DNA chain.
  3. After the DNA synthesis is complete, the 2-cyanoethyl protecting group is easily removed, typically using a mild base, to reveal the free 5'-hydroxyl group.
  4. The use of the 2-cyanoethyl protecting group is crucial in ensuring the fidelity and efficiency of DNA synthesis, as it allows for the precise control of the reaction conditions.
  5. The 2-cyanoethyl group is compatible with the standard phosphoramidite chemistry used in automated DNA synthesizers, making it a widely adopted and essential tool in the field of DNA synthesis.

Review Questions

  • Explain the role of the 2-cyanoethyl group in the context of DNA synthesis.
    • The 2-cyanoethyl group is a critical protecting group used in DNA synthesis to safeguard the 5'-hydroxyl group of nucleosides. By temporarily masking this reactive group, the 2-cyanoethyl group prevents unwanted side reactions and allows for the controlled addition of nucleotides to the growing DNA chain. This precise control is essential for ensuring the fidelity and efficiency of the DNA synthesis process, as it enables the careful manipulation of reaction conditions required for the successful construction of DNA molecules.
  • Describe the advantages of using the 2-cyanoethyl group as a protecting group in DNA synthesis.
    • The 2-cyanoethyl group offers several advantages in the context of DNA synthesis. Firstly, the cyano group provides stability and compatibility with the standard phosphoramidite chemistry used in automated DNA synthesizers, ensuring seamless integration with the established protocols. Secondly, the ease of removal of the 2-cyanoethyl group, typically using a mild base, allows for the final deprotection step without compromising the integrity of the synthesized DNA. Additionally, the use of this protecting group enables the precise control of reaction conditions, which is crucial for maintaining the fidelity and efficiency of the DNA synthesis process, ultimately contributing to the successful construction of desired DNA molecules.
  • Evaluate the significance of the 2-cyanoethyl group in the broader context of nucleic acid synthesis and its impact on advancements in the field.
    • The 2-cyanoethyl group has played a pivotal role in the advancement of nucleic acid synthesis, particularly in the field of DNA synthesis. Its widespread adoption as a protecting group has been instrumental in enabling the development of automated DNA synthesizers and the subsequent surge in the production of synthetic DNA molecules. By providing a reliable and efficient means of controlling the addition of nucleotides, the 2-cyanoethyl group has been a key contributor to the increased accessibility and affordability of DNA synthesis, ultimately facilitating breakthroughs in various areas of biotechnology, genetic engineering, and molecular biology. The versatility and effectiveness of the 2-cyanoethyl group have made it an indispensable tool in the arsenal of modern nucleic acid synthesis, paving the way for further advancements and innovations in the field.