Home Amines 997-68-2
997-68-2,MFCD00056743
Catalog No.:AA01CCHM

997-68-2 | L-Glutamic acid, N-[(5S)-5-amino-5-carboxypentyl]-

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1mg
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  • Technical Information
  • Properties
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Technical Information
Catalog Number:
AA01CCHM
Chemical Name:
L-Glutamic acid, N-[(5S)-5-amino-5-carboxypentyl]-
CAS Number:
997-68-2
Molecular Formula:
C11H20N2O6
Molecular Weight:
276.2863
MDL Number:
MFCD00056743
SMILES:
OC(=O)CC[C@@H](C(=O)O)NCCCC[C@@H](C(=O)O)N
Properties
Computed Properties
 
Complexity:
320  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
2  
Heavy Atom Count:
19  
Hydrogen Bond Acceptor Count:
8  
Hydrogen Bond Donor Count:
5  
Rotatable Bond Count:
11  
XLogP3:
-5.5  

Literature

Title: Potential role for saccharopine reductase in swainsonine metabolism in endophytic fungus, Undifilum oxytropis.

Journal: Fungal biology 20120801

Title: Supporting role of lysine 13 and glutamate 16 in the acid-base mechanism of saccharopine dehydrogenase from Saccharomyces cerevisiae.

Journal: Archives of biochemistry and biophysics 20120601

Title: Lysine catabolism in Haemonchus contortus and Teladorsagia circumcincta.

Journal: Experimental parasitology 20120501

Title: Lysine degradation through the saccharopine pathway in bacteria: LKR and SDH in bacteria and its relationship to the plant and animal enzymes.

Journal: FEBS letters 20120323

Title: Mutation of OsALDH7 causes a yellow-colored endosperm associated with accumulation of oryzamutaic acid A in rice.

Journal: Planta 20120201

Title: Evidence in support of lysine 77 and histidine 96 as acid-base catalytic residues in saccharopine dehydrogenase from Saccharomyces cerevisiae.

Journal: Biochemistry 20120131

Title: The proteome of cytosolic lipid droplets isolated from differentiated Caco-2/TC7 enterocytes reveals cell-specific characteristics.

Journal: Biology of the cell 20111101

Title: A QM/MM-based computational investigation on the catalytic mechanism of saccharopine reductase.

Journal: Molecules (Basel, Switzerland) 20111012

Title: Contribution of K99 and D319 to substrate binding and catalysis in the saccharopine dehydrogenase reaction.

Journal: Archives of biochemistry and biophysics 20111001

Title: The oxidation state of active site thiols determines activity of saccharopine dehydrogenase at low pH.

Journal: Archives of biochemistry and biophysics 20110915

Title: Lysine α-ketoglutarate reductase, but not saccharopine dehydrogenase, is subject to substrate inhibition in pig liver.

Journal: Nutrition research (New York, N.Y.) 20110701

Title: Therapeutic modulation of cerebral L-lysine metabolism in a mouse model for glutaric aciduria type I.

Journal: Brain : a journal of neurology 20110101

Title: Unexpected accumulation of ncm(5)U and ncm(5)S(2) (U) in a trm9 mutant suggests an additional step in the synthesis of mcm(5)U and mcm(5)S(2)U.

Journal: PloS one 20110101

Title: Effects of abiotic stress on plants: a systems biology perspective.

Journal: BMC plant biology 20110101

Title: Amino acids biosynthesis and nitrogen assimilation pathways: a great genomic deletion during eukaryotes evolution.

Journal: BMC genomics 20110101

Title: Differences in transcriptional regulatory mechanisms functioning for free lysine content and seed storage protein accumulation in rice grain.

Journal: Plant & cell physiology 20101201

Title: A molecular probe for Basidiomycota: the spermidine synthase-saccharopine dehydrogenase chimeric gene.

Journal: FEMS microbiology letters 20101101

Title: Glutamates 78 and 122 in the active site of saccharopine dehydrogenase contribute to reactant binding and modulate the basicity of the acid-base catalysts.

Journal: The Journal of biological chemistry 20100702

Title: Role of vimA in cell surface biogenesis in Porphyromonas gingivalis.

Journal: Microbiology (Reading, England) 20100701

Title: Identification of the 2-hydroxyglutarate and isovaleryl-CoA dehydrogenases as alternative electron donors linking lysine catabolism to the electron transport chain of Arabidopsis mitochondria.

Journal: The Plant cell 20100501

Title: First crystal structure of L-lysine 6-dehydrogenase as an NAD-dependent amine dehydrogenase.

Journal: The Journal of biological chemistry 20100312

Title: Metabolism of lysine in alpha-aminoadipic semialdehyde dehydrogenase-deficient fibroblasts: evidence for an alternative pathway of pipecolic acid formation.

Journal: FEBS letters 20100104

Title: Remobilization of Tol2 transposons in Xenopus tropicalis.

Journal: BMC developmental biology 20100101

Title: Structural and transcriptional analysis of plant genes encoding the bifunctional lysine ketoglutarate reductase saccharopine dehydrogenase enzyme.

Journal: BMC plant biology 20100101

Title: Proteomics of plant pathogenic fungi.

Journal: Journal of biomedicine & biotechnology 20100101

Title: Predicted class-I aminoacyl tRNA synthetase-like proteins in non-ribosomal peptide synthesis.

Journal: Biology direct 20100101

Title: Insights into the mechanism of ligand binding to octopine dehydrogenase from Pecten maximus by NMR and crystallography.

Journal: PloS one 20100101

Title: Cytoplasmic- and extracellular-proteome analysis of Diplodia seriata: a phytopathogenic fungus involved in grapevine decline.

Journal: Proteome science 20100101

Title: Proteomic analysis of fungal host factors differentially expressed by Fusarium graminearum infected with Fusarium graminearum virus-DK21.

Journal: Virus research 20090901

Title: Ustilago maydis spermidine synthase is encoded by a chimeric gene, required for morphogenesis, and indispensable for survival in the host.

Journal: FEMS yeast research 20090901

Title: Chemical mechanism of saccharopine reductase from Saccharomyces cerevisiae.

Journal: Biochemistry 20090630

Title: Characterization of the ABA-regulated global responses to dehydration in Arabidopsis by metabolomics.

Journal: The Plant journal : for cell and molecular biology 20090301

Title: Genetic manipulation of lysine catabolism in maize kernels.

Journal: Plant molecular biology 20090101

Title: A pathway-specific microarray analysis highlights the complex and co-ordinated transcriptional networks of the developing grain of field-grown barley.

Journal: Journal of experimental botany 20090101

Title: Understanding the regulation of aspartate metabolism using a model based on measured kinetic parameters.

Journal: Molecular systems biology 20090101

Title: Structural motifs recurring in different folds recognize the same ligand fragments.

Journal: BMC bioinformatics 20090101

Title: Multiple horizontal gene transfer events and domain fusions have created novel regulatory and metabolic networks in the oomycete genome.

Journal: PloS one 20090101

Title: LKR/SDH plays important roles throughout the tick life cycle including a long starvation period.

Journal: PloS one 20090101

Title: Recent amplification and impact of MITEs on the genome of grapevine (Vitis vinifera L.).

Journal: Genome biology and evolution 20090101

Title: Protein-induced alterations in murine hepatic alpha-aminoadipate delta-semialdehyde synthase activity are mediated posttranslationally.

Journal: Nutrition research (New York, N.Y.) 20081201

Title: Supply of nitrogen can reverse senescence processes and affect expression of genes coding for plastidic glutamine synthetase and lysine-ketoglutarate reductase/saccharopine dehydrogenase.

Journal: Plant biology (Stuttgart, Germany) 20080901

Title: Overall kinetic mechanism of saccharopine dehydrogenase (L-glutamate forming) from Saccharomyces cerevisiae.

Journal: Biochemistry 20080513

Title: Modifying lysine biosynthesis and catabolism in corn with a single bifunctional expression/silencing transgene cassette.

Journal: Plant biotechnology journal 20080101

Title: The hidden universal distribution of amino acid biosynthetic networks: a genomic perspective on their origins and evolution.

Journal: Genome biology 20080101

Title: Histoplasma capsulatum proteome response to decreased iron availability.

Journal: Proteome science 20080101

Title: Crystal structures of ligand-bound saccharopine dehydrogenase from Saccharomyces cerevisiae.

Journal: Biochemistry 20071106

Title: Structural studies of the final enzyme in the alpha-aminoadipate pathway-saccharopine dehydrogenase from Saccharomyces cerevisiae.

Journal: Journal of molecular biology 20071026

Title: High-lysine corn generated by endosperm-specific suppression of lysine catabolism using RNAi.

Journal: Plant biotechnology journal 20070901

Title: Ongoing genome reduction in Mycobacterium ulcerans.

Journal: Emerging infectious diseases 20070701

Title: Determinants of substrate specificity for saccharopine dehydrogenase from Saccharomyces cerevisiae.

Journal: Biochemistry 20070626

Title: A proposed proton shuttle mechanism for saccharopine dehydrogenase from Saccharomyces cerevisiae.

Journal: Biochemistry 20070123

Title: Reactome: a knowledge base of biologic pathways and processes.

Journal: Genome biology 20070101

Title: A semi-quantitative GeLC-MS analysis of temporal proteome expression in the emerging nosocomial pathogen Ochrobactrum anthropi.

Journal: Genome biology 20070101

Title: Unbiased characterization of genotype-dependent metabolic regulations by metabolomic approach in Arabidopsis thaliana.

Journal: BMC systems biology 20070101

Title: Reconstruction and flux analysis of coupling between metabolic pathways of astrocytes and neurons: application to cerebral hypoxia.

Journal: Theoretical biology & medical modelling 20070101

Title: Overall kinetic mechanism of saccharopine dehydrogenase from Saccharomyces cerevisiae.

Journal: Biochemistry 20061003

Title: Transcriptional and bioinformatic analysis of the 56.8 kb DNA region amplified in tandem repeats containing the penicillin gene cluster in Penicillium chrysogenum.

Journal: Fungal genetics and biology : FG & B 20060901

Title: Novel lysine biosynthetic gene sequences (LYS1 and LYS5) used as PCR targets for the detection of the pathogenic Candida yeast.

Journal: Applied microbiology and biotechnology 20060901

Title: Lysine catabolism, an effective versatile regulator of lysine level in plants.

Journal: Amino acids 20060301

Title: Functional analysis through site-directed mutations and phylogeny of the Candida albicans LYS1-encoded saccharopine dehydrogenase.

Journal: Molecular genetics and genomics : MGG 20060101

Title: Origin and evolution of the peroxisomal proteome.

Journal: Biology direct 20060101

Title: Crystal structure of the his-tagged saccharopine reductase from Saccharomyces cerevisiae at 1.7-A resolution.

Journal: Cell biochemistry and biophysics 20060101

Title: The alpha-aminoadipate pathway for lysine biosynthesis in fungi.

Journal: Cell biochemistry and biophysics 20060101

Title: The lysine-ketoglutarate reductase-saccharopine dehydrogenase is involved in the osmo-induced synthesis of pipecolic acid in rapeseed leaf tissues.

Journal: Plant physiology and biochemistry : PPB 20060101

Title: Lysine is catabolized to 2-aminoadipic acid in Penicillium chrysogenum by an omega-aminotransferase and to saccharopine by a lysine 2-ketoglutarate reductase. Characterization of the omega-aminotransferase.

Journal: Molecular genetics and genomics : MGG 20051001

Title: Isolation and characterization of enzymes involved in lysine catabolism from sorghum seeds.

Journal: Journal of agricultural and food chemistry 20050309

Title: Regulation of lysine catabolism in Arabidopsis through concertedly regulated synthesis of the two distinct gene products of the composite AtLKR/SDH locus.

Journal: Journal of experimental botany 20050201

Title: Novel chimeric spermidine synthase-saccharopine dehydrogenase gene (SPE3-LYS9) in the human pathogen Cryptococcus neoformans.

Journal: Eukaryotic cell 20040601

Title: Regulation of maize lysine metabolism and endosperm protein synthesis by opaque and floury mutations.

Journal: European journal of biochemistry 20031201

Title: Synthesis of the Arabidopsis bifunctional lysine-ketoglutarate reductase/saccharopine dehydrogenase enzyme of lysine catabolism is concertedly regulated by metabolic and stress-associated signals.

Journal: Plant physiology 20031101

Title: Interdomain communications in bifunctional enzymes: how are different activities coordinated?

Journal: IUBMB life 20030801

Title: Nutritional biochemistry: A new redox-cofactor vitamin for mammals.

Journal: Nature 20030424

Title: Impact of the cross-pathway control on the regulation of lysine and penicillin biosynthesis in Aspergillus nidulans.

Journal: Current genetics 20030101

Title: Isolation of the bifunctional enzyme lysine 2-oxoglutarate reductase-saccharopine dehydrogenase from Phaseolus vulgaris.

Journal: Amino acids 20030101

Title: The activity of the Arabidopsis bifunctional lysine-ketoglutarate reductase/saccharopine dehydrogenase enzyme of lysine catabolism is regulated by functional interaction between its two enzyme domains.

Journal: The Journal of biological chemistry 20021220

Title: The bifunctional LKR/SDH locus of plants also encodes a highly active monofunctional lysine-ketoglutarate reductase using a polyadenylation signal located within an intron.

Journal: Plant physiology 20020901

Title: Analysis of the aspartic acid metabolic pathway using mutant genes.

Journal: Amino acids 20020101

Title: A T-DNA insertion knockout of the bifunctional lysine-ketoglutarate reductase/saccharopine dehydrogenase gene elevates lysine levels in Arabidopsis seeds.

Journal: Plant physiology 20010801

Title: Lysine catabolism: a stress and development super-regulated metabolic pathway.

Journal: Current opinion in plant biology 20010601

Title: The essential amino acid lysine acts as precursor of glutamate in the mammalian central nervous system.

Journal: FEBS letters 20010112

Title: Lysine metabolism in higher plants.

Journal: Amino acids 20010101

Title: Zhou J, et, al. The lysine catabolite saccharopine impairs development by disrupting mitochondrial homeostasis. J Cell Biol. 2019 Feb 4;218(2):580-597.

Title: Leandro J, et, al. Saccharopine, a lysine degradation intermediate, is a mitochondrial toxin. J Cell Biol. 2019 Feb 4;218(2):391-392.

Title: Papes F, et, al. Lysine degradation through the saccharopine pathway in mammals: involvement of both bifunctional and monofunctional lysine-degrading enzymes in mouse. Biochem J. 1999 Dec 1;344 Pt 2(Pt 2):555-63.

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Tags:997-68-2 Molecular Formula|997-68-2 MDL|997-68-2 SMILES|997-68-2 L-Glutamic acid, N-[(5S)-5-amino-5-carboxypentyl]-