Determination and stereochemistry of proteinogenic and non-proteinogenic amino acids in Saudi Arabian date fruits.

Amino Acids

Department of Food Science and Nutrition, College of Food Science and Agriculture, King Saud University, P.O. Box 2460, Riyadh, 11451, Kingdom of Saudi Arabia.

Published: September 2014

AI Article Synopsis

  • The study explores the presence of non-proteinogenic amino acids (AAs) in the edible fruits of the date palm (Phoenix dactylifera L.), highlighting the lack of prior research in this area compared to common proteinogenic AAs.
  • Twelve cultivars of date fruits were analyzed using advanced techniques like automated ion-exchange chromatography and GC-MS, revealing the presence of several non-proteinogenic AAs in varying amounts, such as 5-hydroxypipecolic acid and 1-aminocyclopropane-1-carboxylic acid.
  • The research also includes enantiomeric analysis, finding very low levels of D-amino acids relative to their L-counterparts, and discusses the

Article Abstract

Whereas an abundance of literature is available on the occurrence of common proteinogenic amino acids (AAs) in edible fruits of the date palm (Phoenix dactylifera L.), recent reports on non-proteinogenic (non-coded) AAs and amino components are scarce. With emphasis on these components we have analyzed total hydrolysates of twelve cultivars of date fruits using automated ion-exchange chromatography, HPLC employing a fluorescent aminoquinolyl label, and GC-MS of total hydrolysates using the chiral stationary phases Chirasil(®)-L-Val and Lipodex(®) E. Besides common proteinogenic AAs, relatively large amounts of the following non-proteinogenic amino acids were detected: (2S,5R)-5-hydroxypipecolic acid (1.4-4.0 g/kg dry matter, DM), 1-aminocyclopropane-1-carboxylic acid (1.3-2.6 g/kg DM), γ-amino-n-butyric acid (0.5-1.2 g/kg DM), (2S,4R)-4-hydroxyproline (130-230 mg/kg DM), L-pipecolic acid (40-140 mg/kg DM), and 2-aminoethanol (40-160 mg/kg DM) as well as low or trace amounts (<70 mg/kg DM) of L-ornithine, 5-hydroxylysine, β-alanine, and in some samples (<20 mg/kg DM) of (S)-β-aminoisobutyric acid and (<10 mg/kg DM) L-allo-isoleucine. In one date fruit, traces of α-aminoadipic acid could be determined. Enantiomeric analysis of 6 M DCl/D2O hydrolysates of AAs using chiral capillary gas chromatography-mass spectrometry revealed the presence of very low amounts of D-Ala, D-Asp, D-Glu, D-Ser and D-Phe (1.2-0.4%, relative to the corresponding L-enantiomers), besides traces (0.2-1%) of other D-AAs. The possible relevance of non-proteinogenic amino acids in date fruits is briefly addressed.

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http://dx.doi.org/10.1007/s00726-014-1770-7DOI Listing

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