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Updated: Jun 19, 2026
09:14
Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
An efficient method for the preparation of peptide alcohols
Alan Roy Katritzky1, Nader Elmaghwry Abo-Dya, Srinivasa Rao Tala
1Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA. katritzky@chem.ufl.edu
Organic & Biomolecular Chemistry
|October 16, 2009
Summary
Researchers synthesized N-protected dipeptide and tripeptide alcohols using novel benzotriazole derivatives. This method efficiently produces chiral peptide alcohols with complete retention of stereochemistry.
Area of Science:
- Organic Chemistry
- Peptide Chemistry
Background:
- Benzotriazole derivatives are versatile reagents in organic synthesis.
- Chiral peptide alcohols are important building blocks in medicinal chemistry.
Purpose of the Study:
- To develop a new synthetic route for N-protected dipeptide and tripeptide alcohols.
- To achieve high yields and complete retention of chirality in the synthesis.
Main Methods:
- Treatment of various amino alcohols with N-protected(alpha-aminoacyl)benzotriazoles and N-protected(alpha-dipeptidoyl)benzotriazoles.
- Utilizing specific benzotriazole derivatives (1a-c, 1f-m, 5a, 5b) for peptide bond formation.
Main Results:
- Successful synthesis of N-protected LL-dipeptide alcohols (3a-p) and tripeptide alcohols (6a-c).
- Achieved good yields for the synthesized compounds.
- Demonstrated complete retention of chirality throughout the synthesis.
Conclusions:
- The developed method provides an efficient and stereoselective route to chiral peptide alcohols.
- N-protected(alpha-aminoacyl)benzotriazoles and N-protected(alpha-dipeptidoyl)benzotriazoles are effective reagents for synthesizing peptide alcohols.
- This methodology is valuable for accessing chiral peptide building blocks for further applications.
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