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Search Results (3)

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Keywords = DAACPs

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8 pages, 1590 KiB  
Article
Separation of D-Amino Acid-Containing Tripeptide L-Asn-D-Trp-L-Phe-NH2 and Its Diastereomer Using Crown–Ether-Type Chiral Stationary Phase
by Batsaikhan Mijiddorj, Yohei Kayano, Hiroki Yamagishi, Haruto Nakajima and Izuru Kawamura
Separations 2025, 12(3), 67; https://doi.org/10.3390/separations12030067 - 10 Mar 2025
Viewed by 171
Abstract
Several D-amino acid residue-containing peptides (DAACPs) with antimicrobial, cardio-excitatory, and neuronal activities have been identified in various species. The L-Asn-D-Trp-L-Phe-NH2 (N(dW)F) tripeptide, derived from Aplysia kurodai, exhibits cardiac activity in invertebrates. The chirality of the tryptophan residue at the second position [...] Read more.
Several D-amino acid residue-containing peptides (DAACPs) with antimicrobial, cardio-excitatory, and neuronal activities have been identified in various species. The L-Asn-D-Trp-L-Phe-NH2 (N(dW)F) tripeptide, derived from Aplysia kurodai, exhibits cardiac activity in invertebrates. The chirality of the tryptophan residue at the second position in N(dW)F influences its conformation and biological characteristics. We demonstrated the chiral separation of N(dW)F and its diastereomer NWF using (S)-3,3′-diphenyl-1,1′-binaphthyl-20-crown-6-ether columns (CR-I(+)). A reduction in the ratio of acetonitrile and methanol in the mobile phase allowed the complete separation of N(dW)F and its diastereomer, improving the separation factor (α) from 0.96 to 6.28. Molecular dynamics simulations revealed that the interaction of N(dW)F with CR-I(−) was more favorable than with CR-I(+). These findings indicate that the structure of the CR-I column stereoselectively recognizes peptides and facilitates the separation of naturally occurring D-amino acid residue-containing tripeptides. Full article
(This article belongs to the Special Issue Peptide Synthesis, Separation and Purification)
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10 pages, 2701 KiB  
Article
Characterizing the D-Amino Acid Position in Peptide Epimers by Using Higher-Energy Collisional Dissociation Tandem Mass Spectrometry: A Case Study of Liraglutide
by Yuan-Chih Chen, Hsin-Yi Wu, Lung-Cheng Lin, Chih-Wei Chang and Pao-Chi Liao
Int. J. Mol. Sci. 2024, 25(3), 1379; https://doi.org/10.3390/ijms25031379 - 23 Jan 2024
Viewed by 1827
Abstract
D-amino acid-containing peptides (DAACPs) occur in biological and artificial environments. Since the importance of DAACPs has been recognized, various mass spectrometry-based analytical approaches have been developed. However, the capability of higher-energy collisional dissociation (HCD) fragmentation to characterize DAACP sites has not been evaluated. [...] Read more.
D-amino acid-containing peptides (DAACPs) occur in biological and artificial environments. Since the importance of DAACPs has been recognized, various mass spectrometry-based analytical approaches have been developed. However, the capability of higher-energy collisional dissociation (HCD) fragmentation to characterize DAACP sites has not been evaluated. In this study, we compared the normalized spectra intensity under different conditions of HCD and used liraglutide along with its DAACPs as examples. Our results indicated that the difference in the intensity of y ions between DAACPs and all-L liraglutide could not only distinguish them but also localize the sites of D-amino acids in the DAACPs. Our data demonstrate the potential of using HCD for the site characterization of DAACPs, which may have great impact in biological studies and peptide drug development. Full article
(This article belongs to the Section Physical Chemistry and Chemical Physics)
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14 pages, 1270 KiB  
Review
D-Amino Acids and D-Amino Acid-Containing Peptides: Potential Disease Biomarkers and Therapeutic Targets?
by Mohamed Abdulbagi, Liya Wang, Orwa Siddig, Bin Di and Bo Li
Biomolecules 2021, 11(11), 1716; https://doi.org/10.3390/biom11111716 - 18 Nov 2021
Cited by 61 | Viewed by 7747
Abstract
In nature, amino acids are found in two forms, L and D enantiomers, except for glycine which does not have a chiral center. The change of one form to the other will lead to a change in the primary structure of proteins and [...] Read more.
In nature, amino acids are found in two forms, L and D enantiomers, except for glycine which does not have a chiral center. The change of one form to the other will lead to a change in the primary structure of proteins and hence may affect the function and biological activity of proteins. Indeed, several D-amino acid-containing peptides (DAACPs) were isolated from patients with cataracts, Alzheimer’s and other diseases. Additionally, significant levels of free D-amino acids were found in several diseases, reflecting the disease conditions. Studying the molecular mechanisms of the DAACPs formation and the alteration in D-amino acids metabolism will certainly assist in understanding these diseases and finding new biomarkers and drug targets. In this review, the presence of DAACPs and free D-amino acids and their links with disease development and progress are summarized. Similarly, we highlight some recent advances in analytical techniques that led to improvement in the discovery and analysis of DAACPs and D-amino acids. Full article
(This article belongs to the Section Biomacromolecules: Proteins, Nucleic Acids and Carbohydrates)
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