Influence of pH on the acylation of L-hydroxyproline with palmitoyl chloride in an aqueous acetone medium


Citation

Hoong Seng Soi, . and Mohd Azmil Mohd Noor, . and Rosnah Ismail, . and Zainab Idris, . and Yeong Shoot Kian, . and Hazimah Abu Hassan, . Influence of pH on the acylation of L-hydroxyproline with palmitoyl chloride in an aqueous acetone medium. pp. 288-292.

Abstract

Acylation reactions under Schotten-Bauman condition depend largely on the pH of the reaction medium. When the pH of the reaction medium was 9.0-10.0 the acylation of 0.1 mol of hydroxyproline with 2.5 mol of palmitoyl chloride in an aqueous acetone medium gave O-palmitoyl hydroxyproline and palmitic acid. In another reaction at a pH of 10.5-13.0 a small portion of the formed O-palmitoyl hydroxyproline was converted into N O-di-palmitoyl hydroxyproline which is only between the range of 4.79 to 10.78. However at more higher pH values the N-acylation reaction competed with hydrolysis of the formed O-palmitoyl hydroxyproline to regenerate palmitic acid and L-hydroxyproline which resulted in the reduction of percentage of N O-di-palmitoyl hydroxyproline of 9.00.


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Abstract

Acylation reactions under Schotten-Bauman condition depend largely on the pH of the reaction medium. When the pH of the reaction medium was 9.0-10.0 the acylation of 0.1 mol of hydroxyproline with 2.5 mol of palmitoyl chloride in an aqueous acetone medium gave O-palmitoyl hydroxyproline and palmitic acid. In another reaction at a pH of 10.5-13.0 a small portion of the formed O-palmitoyl hydroxyproline was converted into N O-di-palmitoyl hydroxyproline which is only between the range of 4.79 to 10.78. However at more higher pH values the N-acylation reaction competed with hydrolysis of the formed O-palmitoyl hydroxyproline to regenerate palmitic acid and L-hydroxyproline which resulted in the reduction of percentage of N O-di-palmitoyl hydroxyproline of 9.00.

Additional Metadata

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Item Type: Article
AGROVOC Term: Acylation
AGROVOC Term: Acetone
AGROVOC Term: Chemical reactions
AGROVOC Term: Hydrolysis
AGROVOC Term: Filtration
AGROVOC Term: Stirring
AGROVOC Term: Gas chromatography
AGROVOC Term: Acidification
AGROVOC Term: Hydroxyproline
AGROVOC Term: Amino acids
Depositing User: Ms. Suzila Mohamad Kasim
Last Modified: 24 Apr 2025 06:28
URI: http://webagris.upm.edu.my/id/eprint/24335

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