d-Amino acids in mammals and their diagnostic value

Hamase, Kenji; Morikawa, Akiko; Zaitsu, Kiyoshi

doi:10.1016/s1570-0232(02)00690-6

Cited by 196 publications

(152 citation statements)

References 144 publications

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“…Generally, only L-amino acids are susceptible to enzyme-catalyzed polymerization (translation) to structural and functional peptides and proteins in mammals (Friedmann, 1999). Recent progress in analytical chemistry, however, has enabled the sensitive and selective determination of D-amino acids in mammalian tissues and revealed that substantial amounts of D-amino acids are present in mammals (Hamase et al, 2002). The function and origin of D-amino acids has been investigated in the last decades, but only for D-serine and D-aspartate relevant functional roles have been identified (Wang et al, 2000;Snyder and Kim, 2000).…”

Section: Introductionmentioning

confidence: 99%

Preferred Stereoselective Transport of the D-isomer of cis-4-[¹⁸F]fluoro-proline at the Blood–Brain Barrier

Langen

Hamacher

Bauer

et al. 2005

J Cereb Blood Flow Metab

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Generally, L-amino acids are preferably transported into mammalian cells compared with their D-isomers, and only L-amino acids are incorporated into proteins. Former studies, however, indicated that D-[H]proline is accumulated in the brain of mice after injection, while L-[ 3 H]proline is not. We investigated the differential cerebral uptake of the D-and L-isomers of the PET tracer cis-4-in rats by dual tracer autoradiography and the uptake of D-cis-FPro in two human subjects by PET. The standardized uptake value (SUV) of D-cis-FPro in the cerebral cortex of rats 2 h p.i. was 3.0571.18 (n ¼ 9) versus 0.0670.01 (n ¼ 4) for L-cis-FPro (Po0.001) and 1.2970.27 (n ¼ 4) for D-Pro versus 0.3070.14 (n ¼ 9) for L-Pro (Po0.001). Analysis of the rat brain tissue after injection of D-cis-FPro (n ¼ 3) revealed no radioactivity in the proteins but a relevant part in the form of L-trans-FPro. The PET studies yielded a four-to five-fold higher SUV and influx rate constant in the human cortex for D-cis-FPro than for Lcis-FPro. We conclude that D-cis-FPro and D-Pro are preferably transported at the blood-brain barrier compared with their L-isomers and isomerized to the L-form within the brain. Thus, D-Pro in the plasma might be a source of intracerebral L-proline, which has been shown to act as a modulator of excitatory neurotransmission.

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Section: Introductionmentioning

confidence: 99%

Preferred Stereoselective Transport of the D-isomer of cis-4-[¹⁸F]fluoro-proline at the Blood–Brain Barrier

Langen

Hamacher

Bauer

et al. 2005

J Cereb Blood Flow Metab

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“…Table 1. D-AAs related to some diseases described previously [43]. Ala: alanine; Asp: aspartic acid; Ser: serine; Asx: asparagine/aspartic acid; Pro: proline.…”

Section: D-amino Acids As Biomarkers Of Diseases/disordersmentioning

confidence: 98%

“…Ultra-high performance liquid chromatography methods for the determination and analysis of disease biomarkers including some chiral methods for AAs were clearly reviewed [41]. Several review papers focused on the presence of D-AAs in mammals, their function, their diagnostic value as biomarkers, and also HPLC methods for their determination [42][43][44][45][46][47]. Examples of D-AAs related to some diseases are summarized in Table 1.The enantioseparation of D,L-AAs continues to be a subject of immense study due to its significant importance in various areas.…”

Section: D-amino Acids As Biomarkers Of Diseases/disordersmentioning

confidence: 99%

Enantiomeric Ratio of Amino Acids as a Tool for Determination of Aging and Disease Diagnostics by Chromatographic Measurement

2016

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Abstract:Occurrence of D-amino acids in living organisms is a useful indicator of various changes, diseases, or disorders. Determination of amino acid enantiomers, namely the enantiomeric ratio of amino acids or excess of certain D-amino acids, represents a useful tool in the studies of aging processes or biomarkers in disease/disorder diagnosis in humans. The amount of D-amino acids is usually very low. Therefore, suitable sample pretreatment, often derivatization, and highly selective and sensitive separation methods are essential for D-amino acid analysis in this field. Chromatographic techniques offer appropriate choices for solving these tasks. This review covers the advances in methodology and development of improved instrumental chromatographic methods focused on D,L-amino acid separation and determination. New findings in the area of possible D-amino acid biomarkers are also included.

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“…In particular, free D-Asp, D-Ser and D-Ala are found in mammalian tissues, and their physiological roles are being investigated. D-Asp is observed in various endocrine and neuroendocrine tissues and regulates the hormonal synthesis and secretion in tissues [22]. D-Ser is also localized to the frontal brain areas and regulates…”

Section: Determination Of Dl-amino Acids In Human Fingernail Of Diabementioning

confidence: 99%

Development of the High Sensitive Separation Analysis Method of Metabolites in Human Nail and its Application to the Diagnosis of Chronic Disease

Min

2014

Chromatography

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This review summarizes the possibility to diagnosing the chronic diseases and application of determination of metabolites of the noninvasive human nails. A target derivatization UPLC-ESI-MS method is a powerful tool for the analysis of bioactive compounds with high sensitivity and selectivity. We developed target derivatization UPLC-ESI-MS methods to analyze the biological trace components in human fingernail. Moreover, we have used these methods to detect the metabolites in human fingernails, such as DL-amino acids, polyamines and Advanced Glycation End products (AGEs). Through detecting the biological trace components in the real samples from human, we tested the possibility to use these new methods to diagnosing the chronic diseases, i.e., diabetes, lung cancer. Some applications utilizing these target derivatization methods for the analyses determination of metabolites in the human fingernails are also described in this paper.

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d-Amino acids in mammals and their diagnostic value

Cited by 196 publications

References 144 publications

Preferred Stereoselective Transport of the D-isomer of cis-4-[¹⁸F]fluoro-proline at the Blood–Brain Barrier

Preferred Stereoselective Transport of the D-isomer of cis-4-[¹⁸F]fluoro-proline at the Blood–Brain Barrier

Enantiomeric Ratio of Amino Acids as a Tool for Determination of Aging and Disease Diagnostics by Chromatographic Measurement

Development of the High Sensitive Separation Analysis Method of Metabolites in Human Nail and its Application to the Diagnosis of Chronic Disease

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d-Amino acids in mammals and their diagnostic value

Cited by 196 publications

References 144 publications

Preferred Stereoselective Transport of the D-isomer of cis-4-[18F]fluoro-proline at the Blood–Brain Barrier

Preferred Stereoselective Transport of the D-isomer of cis-4-[18F]fluoro-proline at the Blood–Brain Barrier

Enantiomeric Ratio of Amino Acids as a Tool for Determination of Aging and Disease Diagnostics by Chromatographic Measurement

Development of the High Sensitive Separation Analysis Method of Metabolites in Human Nail and its Application to the Diagnosis of Chronic Disease

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Preferred Stereoselective Transport of the D-isomer of cis-4-[¹⁸F]fluoro-proline at the Blood–Brain Barrier

Preferred Stereoselective Transport of the D-isomer of cis-4-[¹⁸F]fluoro-proline at the Blood–Brain Barrier