A Closer Examination of 6-Aminoquinolyl-N-Hydroxysuccinimidyl Carbamate Amino Acid Derivatization in HPLC with Multiple Detection Modes

Sung, Yu-Sheng; Berthod, Alain; Roy, Daipayan; Armstrong, Daniel W.

doi:10.1007/s10337-021-04051-w

Cited by 7 publications

(3 citation statements)

References 27 publications

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“…Furthermore, AQC AAs derivatives can be stored securely at room temperature and in the dark for up to 3 wks, facilitating analytical testing. Sung et al [88] compared four detection modes (UV detection, FL detection, single ion analysis, and MRM) using the same kit. After derivatization, the derivative mass of AAs increased by 170 Da, avoiding detection in the low mass region and generating a positive charge, which facilitates ionization.…”

Section: Hplc Tandem Msmentioning

confidence: 99%

Overview of chromatographic and electrophoretic methods for the determination of branched‐chain amino acids

Yin

Adams

Schepdael

2023

J of Separation Science

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The significance of branched‐chain amino acids in diseases was clearly shown over the years. This review aims to describe the available techniques for their analytical determination. The article provides examples of the use of various analytical methods. The methods are divided into two categories: derivatization and non‐derivatization approaches. Separation is achieved through different chromatography or capillary electrophoresis techniques and can be combined with different detectors such as flame ionization, ultraviolet, fluorescence, and mass spectrometry. It compares the application of various derivatization reagents or detection as such for different detectors.

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Section: Hplc Tandem Msmentioning

confidence: 99%

Overview of chromatographic and electrophoretic methods for the determination of branched‐chain amino acids

Yin

Adams

Schepdael

2023

J of Separation Science

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“…This is the principle of the Marfey method [ 17 ]. Classical HPLC, TLC, or GC for volatile derivatized compounds are able to separate the diastereoisomers obtained [ 9 , 18 ]. In modern chiral studies, the derivatization approach has been supplanted by the use of chiral stationary phases (CSPs) which directly separate native molecules, hence avoiding several sample preparation steps.…”

Section: Identifying D-amino Acidsmentioning

confidence: 99%

“…The macrocyclic glycopeptides based CSPs make chiral columns that are especially efficient in separating both native and N-blocked amino acids [ 20 ]. Recently introduced superficially porous particles bonded with chiral selectors allowed to obtain enantiomer separation in a very short time using minute amount of mobile phases [ 8 , 9 , 18 , 19 ]. Associating achiral and chiral columns in 2D-HPLC greatly extended the capacity of the chromatographic methods allowing detecting trace amounts of chiral compounds [ 9 , 18 ].…”

Section: Identifying D-amino Acidsmentioning

confidence: 99%

Occurrence of D-amino acids in natural products

Armstrong,

Berthod

2023

Nat. Prod. Bioprospect.

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Since the identified standard genetic code contains 61 triplet codons of three bases for the 20 L-proteinogenic amino acids (AAs), no D-AA should be found in natural products. This is not what is observed in the living world. D-AAs are found in numerous natural compounds produced by bacteria, algae, fungi, or marine animals, and even vertebrates. A review of the literature indicated the existence of at least 132 peptide natural compounds in which D-AAs are an essential part of their structure. All compounds are listed, numbered and described herein. The two biosynthetic routes leading to the presence of D-AA in natural products are: non-ribosomal peptide synthesis (NRPS), and ribosomally synthesized and post-translationally modified peptide (RiPP) synthesis which are described. The methods used to identify the AA chirality within naturally occurring peptides are briefly discussed. The biological activity of an all-L synthetic peptide is most often completely different from that of the D-containing natural compounds. Analyzing the selected natural compounds showed that D-Ala, D-Val, D-Leu and D-Ser are the most commonly encountered D-AAs closely followed by the non-proteinogenic D-allo-Thr. D-Lys and D-Met were the least prevalent D-AAs in naturally occurring compounds. Graphical Abstract

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Enhanced carboxypeptidase efficacies and differentiation of peptide epimers

Sung

Putman

et al. 2022

Analytical Biochemistry

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A Closer Examination of 6-Aminoquinolyl-N-Hydroxysuccinimidyl Carbamate Amino Acid Derivatization in HPLC with Multiple Detection Modes

Cited by 7 publications

References 27 publications

Overview of chromatographic and electrophoretic methods for the determination of branched‐chain amino acids

Overview of chromatographic and electrophoretic methods for the determination of branched‐chain amino acids

Occurrence of D-amino acids in natural products

Enhanced carboxypeptidase efficacies and differentiation of peptide epimers

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