4.3 Review

d-Amino acids in biological systems

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Review Biochemistry & Molecular Biology

Advancing D-amino acid-containing peptide discovery in the metazoan

David H. Mast et al.

Summary: The discovery of enzyme-derived D-amino acid-containing peptides challenges assumptions about the homochirality of animal proteins and presents new analytical challenges in peptide structural and functional characterization. Most known DAACPs have been identified through laborious purification studies or homology to previously identified ones. High throughput mass spectrometry-based peptidomics dominate peptide characterization experiments, with stereochemistry rarely considered due to technical challenges of identifying L/D isomerization, suggesting that more DAACPs remain to be uncovered.

BIOCHIMICA ET BIOPHYSICA ACTA-PROTEINS AND PROTEOMICS (2021)

Article Microbiology

Production of both l- and d- N-acyl-homoserine lactones by Burkholderia cepacia and Vibrio fischeri

Abiud E. Portillo et al.

Summary: Quorum sensing (QS) is a complex process in which molecules like l-N-acyl-homoserine lactones (l-AHLs) allow bacteria to detect cell population density by gene regulation. The study suggests the possibility of a distinct biosynthetic pathway for d-AHL production in bacterial communication.

MICROBIOLOGYOPEN (2021)

Article Infectious Diseases

Biosynthesis and Heterologous Expression of Cacaoidin, the First Member of the Lanthidin Family of RiPPs

Fernando Roman-Hurtado et al.

Summary: This study reports the production of cacaoidin by the strain Streptomyces cacaoi CA-170360, which represents the first member of the new lanthidin RiPP family. The complete identification, cloning, and heterologous expression of the cacaoidin biosynthetic gene cluster were described, revealing unique RiPP genes with unpredicted functions. The cacaoidin pathway is restricted to specific strains of the subspecies Streptomyces cacaoi, and other potential class V lanthipeptide pathways were also identified in public genome databases.

ANTIBIOTICS-BASEL (2021)

Article Multidisciplinary Sciences

D-cysteine is an endogenous regulator of neural progenitor cell dynamics in the mammalian brain

Evan R. Semenza et al.

Summary: D-cysteine, as an endogenous molecule in the mammalian brain, is involved in regulating the proliferation of neural progenitor cells and may play a role in NPC homeostasis during brain development.

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA (2021)

Review Chemistry, Multidisciplinary

Racemases and epimerases operating through a 1,1-proton transfer mechanism: reactivity, mechanism and inhibition

Matthew D. Lloyd et al.

Summary: Racemases and epimerases are important enzymes in biotechnology and drug research, with potential applications. Research focuses on their catalytic mechanisms and development of corresponding inhibitors, including rational design of inhibitors and development of transition-state mimics.

CHEMICAL SOCIETY REVIEWS (2021)

Article Chemistry, Multidisciplinary

Identification of the peptide epimerase MslH responsible for d-amino acid introduction at the C-terminus of ribosomal peptides

Zhi Feng et al.

Summary: This study reveals the identification of MslH as a novel epimerase involved in the post-translational epimerization of the C-terminal Trp residue of the precursor peptide MslA, showing opportunities in peptide bioengineering.

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Enantiomeric separation of quorum sensing autoinducer homoserine lactones using GC-MS and LC-MS

Elizabeth Readel et al.

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Cacaoidin, First Member of the New Lanthidin RiPP Family

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ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

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Stimulation of root growth and enhanced nitrogenous metabolite content in habanero pepper (Capsicum chinense Jacq.) treated with a d-amino acid mixture

Angelica Anahi Serralta-Interian et al.

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Review Microbiology

Regulation of peptidoglycan synthesis and remodelling

Alexander J. F. Egan et al.

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Review Biochemistry & Molecular Biology

D-Amino Acids in Plants: Sources, Metabolism, and Functions

Uener Kolukisaoglu

INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES (2020)

Review Biochemistry & Molecular Biology

Advances in D-Amino Acids in Neurological Research

James M. Seckler et al.

INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES (2020)

Review Biochemistry & Molecular Biology

D-Aspartic Acid in Vertebrate Reproduction: Animal Models and Experimental Designs

Maria Maddalena Di Fiore et al.

BIOMOLECULES (2019)

Review Nutrition & Dietetics

d-amino Acids in Health and Disease: A Focus on Cancer

Jacco J. A. J. Bastings et al.

NUTRIENTS (2019)

Article Biology

Sex hormone levels in the brain of D-aspartate-treated rats

Maria Maddalena Di Fiore et al.

COMPTES RENDUS BIOLOGIES (2018)

Review Chemistry, Analytical

Amino acid racemization and its relation to geochronology and archaeometry

Ardith D. Bravenec et al.

JOURNAL OF SEPARATION SCIENCE (2018)

Article Multidisciplinary Sciences

Method to generate highly stable D-amino acid analogs of bioactive helical peptides using a mirror image of the entire PDB

Michael Garton et al.

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA (2018)

Review Microbiology

Emerging Role of D-Amino Acid Metabolism in the Innate Defense

Jumpei Sasabe et al.

FRONTIERS IN MICROBIOLOGY (2018)

Review Microbiology

Peptide Epimerization Machineries Found in Microorganisms

Yasushi Ogasawara et al.

FRONTIERS IN MICROBIOLOGY (2018)

Article Microbiology

A Broad Spectrum Racemase in Pseudomonas putida KT2440 Plays a Key Role in Amino Acid Catabolism

Atanas D. Radkov et al.

FRONTIERS IN MICROBIOLOGY (2018)

Article Endocrinology & Metabolism

Chronic D-serine supplementation impairs insulin secretion

Lisa Suwandhi et al.

MOLECULAR METABOLISM (2018)

Article Biochemistry & Molecular Biology

Assays of D-Amino Acid Oxidase Activity

Elena Rosini et al.

FRONTIERS IN MOLECULAR BIOSCIENCES (2018)

Article Multidisciplinary Sciences

D-Glutamate is metabolized in the heart mitochondria

Makoto Ariyoshi et al.

SCIENTIFIC REPORTS (2017)

Review Biochemistry & Molecular Biology

An overview on D-amino acids

Giuseppe Genchi

AMINO ACIDS (2017)

Article Pharmacology & Pharmacy

NMDA receptors are important regulators of pancreatic cancer and are potential targets for treatment

William G. North et al.

CLINICAL PHARMACOLOGY-ADVANCES AND APPLICATIONS (2017)

Article Biochemistry & Molecular Biology

D-Amino Acid Levels in Perfused Mouse Brain Tissue and Blood: A Comparative Study

Choyce A. Weatherly et al.

ACS CHEMICAL NEUROSCIENCE (2017)

Article Medicine, General & Internal

Association Between Serum Cystatin C and Creatinine in Chronic Kidney Disease Subjects Attending a Tertiary Health Care Centre

Janice Dsa et al.

JOURNAL OF CLINICAL AND DIAGNOSTIC RESEARCH (2017)

Article Biochemistry & Molecular Biology

Distribution and evolution of the serine/aspartate racemase family in invertebrates

Kouji Uda et al.

AMINO ACIDS (2016)

Review Microbiology

Environmental roles of microbial amino acid racemases

Sara B. Hernandez et al.

ENVIRONMENTAL MICROBIOLOGY (2016)

Article Biochemistry & Molecular Biology

Mechanism of NMDA Receptor Inhibition and Activation

Shujia Zhu et al.

Article Chemistry, Multidisciplinary

Discovery and Characterization of Bicereucin, an Unusual D-Amino Acid-Containing Mixed Two-Component Lantibiotic

Liujie Huo et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Review Microbiology

Biofilms: an emergent form of bacterial life

Hans-Curt Flemming et al.

NATURE REVIEWS MICROBIOLOGY (2016)

Review Pharmacology & Pharmacy

Physiological Roles of Non-Neuronal NMDA Receptors

Adam D. Hogan-Cann et al.

TRENDS IN PHARMACOLOGICAL SCIENCES (2016)

Article Multidisciplinary Sciences

Chiral amino acid metabolomics for novel biomarker screening in the prognosis of chronic kidney disease

Tomonori Kimura et al.

SCIENTIFIC REPORTS (2016)

Article Chemistry, Analytical

Effects of high-salinity seawater acclimation on the levels of D-alanine in the muscle and hepatopancreas of kuruma prawn, Marsupenaeus japonicus

Naoko Yoshikawa et al.

JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS (2015)

Article Biochemistry & Molecular Biology

Characterization of pancreatic NMDA receptors as possible drug targets for diabetes treatment

Jan Marquard et al.

NATURE MEDICINE (2015)

Article Neurosciences

Potent anti-seizure effects of D-leucine

Adam L. Hartman et al.

NEUROBIOLOGY OF DISEASE (2015)

Article Psychiatry

D-serine levels in Alzheimer's disease: implications for novel biomarker development

C. Madeira et al.

TRANSLATIONAL PSYCHIATRY (2015)

Correction Biotechnology & Applied Microbiology

A highly stable D-amino acid oxidase of the thermophilic bacterium Rubrobacter xylanophilus (vol 80, pg 7219, 2014)

Shouji Takahashi et al.

BIOENGINEERED (2015)

Review Biotechnology & Applied Microbiology

Bacterial synthesis of D-amino acids

Atanas D. Radkov et al.

APPLIED MICROBIOLOGY AND BIOTECHNOLOGY (2014)

Article Biochemistry & Molecular Biology

D-Alanine in the islets of Langerhans of rat pancreas

Nobutoshi Ota et al.

BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS (2014)

Review Neurosciences

The Role of Ketamine in Treatment-Resistant Depression: A Systematic Review

Gianluca Serafini et al.

CURRENT NEUROPHARMACOLOGY (2014)

Review Biochemistry & Molecular Biology

Biogenesis of D-amino acid containing peptides/proteins: where, when and how?

Celine Ollivaux et al.

JOURNAL OF PEPTIDE SCIENCE (2014)

Article Chemistry, Multidisciplinary

Structure and Biosynthesis of Carnolysin, a Homologue of Enterococcal Cytolysin with D-Amino Acids

Christopher T. Lohans et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

Review Biochemistry & Molecular Biology

D-amino acid-based peptide inhibitors as early or preventative therapy in Alzheimer disease

Jitendra Kumar et al.

Review Plant Sciences

Shedding light on ethylene metabolism in higher plants

Maria A. Rodrigues et al.

FRONTIERS IN PLANT SCIENCE (2014)

Review Chemistry, Medicinal

Significance of the Natural Occurrence of L- Versus D-Pipecolic Acid: A Review

Valerie Vranova et al.

CHIRALITY (2013)

Review Biochemistry & Molecular Biology

Deregulation of excitatory neurotransmission underlying synapse failure in Alzheimer's disease

Andrea C. Paula-Lima et al.

JOURNAL OF NEUROCHEMISTRY (2013)

Review Neurosciences

NMDA receptor subunit diversity: impact on receptor properties, synaptic plasticity and disease

Pierre Paoletti et al.

NATURE REVIEWS NEUROSCIENCE (2013)

Article Endocrinology & Metabolism

Production of Hydrogen Sulfide from D-Cysteine and Its Therapeutic Potential

Norihiro Shibuya et al.

Frontiers in Endocrinology (2013)

Review Biochemistry & Molecular Biology

Nutritional and medicinal aspects of D-amino acids

Mendel Friedman et al.

AMINO ACIDS (2012)

Article Neurosciences

Contributions of the D-serine pathway to schizophrenia

Viviane Labrie et al.

NEUROPHARMACOLOGY (2012)

Article Biochemistry & Molecular Biology

Uptake and conversion of d-amino acids in Arabidopsis thaliana

Dirk Goerdes et al.

AMINO ACIDS (2011)

Review Biochemistry & Molecular Biology

Emerging knowledge of regulatory roles of d-amino acids in bacteria

Felipe Cava et al.

CELLULAR AND MOLECULAR LIFE SCIENCES (2011)

Article Biochemistry & Molecular Biology

A Novel Pyridoxal 5′-Phosphate-dependent Amino Acid Racemase in the Aplysia californica Central Nervous System

Liping Wang et al.

JOURNAL OF BIOLOGICAL CHEMISTRY (2011)

Review Biochemical Research Methods

D-Amino acid metabolism in mammals: Biosynthesis, degradation and analytical aspects of the metabolic study

Hiroko Ohide et al.

JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES (2011)

Article Biochemical Research Methods

Simultaneous two-dimensional HPLC determination of free D-serine and D-alanine in the brain and periphery of mutant rats lacking D-amino-acid oxidase

Yurika Miyoshi et al.

JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES (2011)

Article Biochemistry & Molecular Biology

Thyroid Hormones and D-Aspartic Acid, D-Aspartate Oxidase, D-Aspartate Racemase, H2O2, and ROS in Rats and Mice

Enza Topo et al.

CHEMISTRY & BIODIVERSITY (2010)

Review Biochemistry & Molecular Biology

Origin, Microbiology, Nutrition, and Pharmacology of D-Amino Acids

Mendel Friedman

CHEMISTRY & BIODIVERSITY (2010)

Article Multidisciplinary Sciences

Aspartate racemase, generating neuronal D-aspartate, regulates adult neurogenesis

Paul M. Kim et al.

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA (2010)

Article Psychiatry

High dose D-serine in the treatment of schizophrenia

Joshua T. Kantrowitz et al.

SCHIZOPHRENIA RESEARCH (2010)

Article Multidisciplinary Sciences

D-Amino Acids Trigger Biofilm Disassembly

Ilana Kolodkin-Gal et al.

SCIENCE (2010)

Article Cell Biology

Biofilms

Daniel Lopez et al.

COLD SPRING HARBOR PERSPECTIVES IN BIOLOGY (2010)

Article Biochemistry & Molecular Biology

Molecular Characterization of Alanine Racemase in the Kuruma Prawn Marsupenaeus japonicus

Naoko Yoshikawa et al.

JOURNAL OF BIOCHEMISTRY (2009)

Article Multidisciplinary Sciences

D-Amino Acids Govern Stationary Phase Cell Wall Remodeling in Bacteria

Hubert Lam et al.

SCIENCE (2009)

Letter Biochemistry & Molecular Biology

D-amino acid oxidase activity and expression are increased in schizophrenia

P. W. J. Burnet et al.

MOLECULAR PSYCHIATRY (2008)

Article Psychiatry

Increased brain D-amino acid oxidase (DAAO) activity in schizophrenia

Caroline Madeira et al.

SCHIZOPHRENIA RESEARCH (2008)

Article Biochemistry & Molecular Biology

D-Serine is a key determinant of glutamate toxicity in amyotrophic lateral sclerosis

Jumpei Sasabe et al.

EMBO JOURNAL (2007)

Article Physiology

Why is D-serine nephrotoxic and α-aminoisobutyric acid protective?

Alexander W. Krug et al.

AMERICAN JOURNAL OF PHYSIOLOGY-RENAL PHYSIOLOGY (2007)

Article Biochemistry & Molecular Biology

Immunohistochemical localizationd D-alanine to β-cells in rat pancreas

Akiko Morikawa et al.

BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS (2007)

Article Plant Sciences

AAP1 transports uncharged amino acids into roots of Arabidopsis

Yong-Hwa Lee et al.

PLANT JOURNAL (2007)

Article Psychiatry

A CSF and postmortem brain study of D-serine metabolic parameters in schizophrenia

Inna Bendikov et al.

SCHIZOPHRENIA RESEARCH (2007)

Article Biotechnology & Applied Microbiology

Overproduction and characterization of a recombinant D-amino acid oxidase from Arthrobacter protophormiae

Birgit Geueke et al.

APPLIED MICROBIOLOGY AND BIOTECHNOLOGY (2007)

Article Biochemistry & Molecular Biology

Molecular and biochemical characterization of a serine racemase from Arabidopsis thaliana

Y Fujitani et al.

PHYTOCHEMISTRY (2006)

Article Cell Biology

D-aspartic acid in the nervous system of Aplysia limacina:: Possible role in neurotransmission

P Spinelli et al.

JOURNAL OF CELLULAR PHYSIOLOGY (2006)

Article Neurosciences

D-alanine added to antipsychotics for the treatment of schizophrenia

GE Tsai et al.

BIOLOGICAL PSYCHIATRY (2006)

Review Biochemistry & Molecular Biology

Pathophysiologically based treatment interventions in schizophrenia

David A. Lewis et al.

NATURE MEDICINE (2006)

Article Endocrinology & Metabolism

Endocrine roles of D-aspartic acid in the testis of lizard Podarcis s. sicula

F Raucci et al.

JOURNAL OF ENDOCRINOLOGY (2005)

Article Biochemistry & Molecular Biology

β-amyloid is different in normal aging and in Alzheimer disease

A Piccini et al.

JOURNAL OF BIOLOGICAL CHEMISTRY (2005)

Article Pharmacology & Pharmacy

Physiological function and metabolism of free D-alanine in aquatic animals

H Abe et al.

BIOLOGICAL & PHARMACEUTICAL BULLETIN (2005)

Review Clinical Neurology

Reduced D-serine to total serine ratio in the cerebrospinal fluid of drug naive schizophrenic patients

K Hashimoto et al.

PROGRESS IN NEURO-PSYCHOPHARMACOLOGY & BIOLOGICAL PSYCHIATRY (2005)

Article Chemistry, Multidisciplinary

Polypeptide chains containing D-γ-hydroxyvaline

K Pisarewicz et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2005)

Article Chemistry, Medicinal

Pharmacokinetics of theanine enantiomers in rats

MJ Desai et al.

CHIRALITY (2005)

Article Biochemistry & Molecular Biology

Post-translational amino acid isomerization - A functionally important D-amino acid in an excitatory peptide

O Buczek et al.

JOURNAL OF BIOLOGICAL CHEMISTRY (2005)

Review Microbiology

Vancomycin resistance in enterococci due to synthesis of precursors terminating in D-Alanyl-D-Serine

PE Reynolds et al.

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY (2005)

Article Biotechnology & Applied Microbiology

A conditional marker gene allowing both positive and negative selection in plants

O Erikson et al.

NATURE BIOTECHNOLOGY (2004)

Article Endocrinology & Metabolism

Testicular endocrine activity is upregulated by D-aspartic acid in the green frog, Rana esculenta

F Raucci et al.

JOURNAL OF ENDOCRINOLOGY (2004)

Review Neurosciences

Unraveling the mechanisms involved in motor neuron degeneration in ALS

LI Bruijn et al.

ANNUAL REVIEW OF NEUROSCIENCE (2004)

Review Chemistry, Medicinal

Opioid receptors and their ligands

A Janecka et al.

CURRENT TOPICS IN MEDICINAL CHEMISTRY (2004)

Review Medicine, General & Internal

Mechanisms of disease - Epilepsy

BS Chang et al.

NEW ENGLAND JOURNAL OF MEDICINE (2003)

Article Biochemistry & Molecular Biology

Stereoselective interactions of peptide inhibitors with the β-amyloid peptide

RJ Chalifour et al.

JOURNAL OF BIOLOGICAL CHEMISTRY (2003)

Article Multidisciplinary Sciences

Genetic and physiological data implicating the new human gene G72 and the gene for D-amino acid oxidase in schizophrenia

I Chumakov et al.

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA (2002)

Review Chemistry, Multidisciplinary

Understanding nature's strategies for enzyme-catalyzed racemization and epimerization

ME Tanner

ACCOUNTS OF CHEMICAL RESEARCH (2002)

Article Endocrinology & Metabolism

Regulatory responses to an oral D-glutamate load: formation of D-pyrrolidone carboxylic acid in humans

D Raj et al.

AMERICAN JOURNAL OF PHYSIOLOGY-ENDOCRINOLOGY AND METABOLISM (2001)

Article Multidisciplinary Sciences

The x-ray structure of D-amino acid oxidase at very high resolution identifies the chemical mechanism of flavin-dependent substrate dehydrogenation

S Umhau et al.

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA (2000)

Review Biochemistry & Molecular Biology

D-Amino acid oxidase: new findings

MS Pilone

CELLULAR AND MOLECULAR LIFE SCIENCES (2000)

Article Biochemistry & Molecular Biology

Isoaspartate formation and neurodegeneration in Alzheimer's disease

T Shimizu et al.

ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS (2000)

Article Biotechnology & Applied Microbiology

Osmoprotection by pipecolic acid in Sinorhizobium meliloti:: Specific effects of D and L isomers

K Gouffi et al.

APPLIED AND ENVIRONMENTAL MICROBIOLOGY (2000)

Article Multidisciplinary Sciences

D-serine is an endogenous ligand for the glycine site of the N-methyl-D-aspartate receptor

JP Mothet et al.

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA (2000)