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56271-99-9 | γ-Carboxy-DL-glutamic acid
CAS No: 56271-99-9 Catalog No: AG003VGF MDL No:
Product Description
Catalog Number:
AG003VGF
Chemical Name:
γ-Carboxy-DL-glutamic acid
CAS Number:
56271-99-9
IUPAC Name:
3-aminopropane-1,1,3-tricarboxylic acid
InChI:
InChI=1S/C6H9NO6/c7-3(6(12)13)1-2(4(8)9)5(10)11/h2-3H,1,7H2,(H,8,9)(H,10,11)(H,12,13)
InChI Key:
UHBYWPGGCSDKFX-UHFFFAOYSA-N
EC Number:
260-087-8
Properties
Complexity:
223
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
191.043g/mol
Formal Charge:
0
Heavy Atom Count:
13
Hydrogen Bond Acceptor Count:
7
Hydrogen Bond Donor Count:
4
Isotope Atom Count:
0
Molecular Weight:
191.139g/mol
Monoisotopic Mass:
191.043g/mol
Rotatable Bond Count:
5
Topological Polar Surface Area:
138A^2
Undefined Atom Stereocenter Count:
1
Undefined Bond Stereocenter Count:
0
XLogP3:
-3.7
Literature
| Title | Journal |
|---|---|
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| Interaction of prothrombin with a phospholipid surface: evidence for a membrane-induced conformational change. | Molecular and cellular biochemistry 20110201 |
| Ca 2+-induced self-assembly in designed peptides with optimally spaced gamma-carboxyglutamic acid residues. | Journal of inorganic biochemistry 20110101 |
| Cross-species gene normalization by species inference. | BMC bioinformatics 20110101 |
| Characterization of γ-carboxylated tryptic peptides by collision-induced dissociation and electron transfer dissociation mass spectrometry. | European journal of mass spectrometry (Chichester, England) 20110101 |
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| Identification of four alternatively spliced transcripts of the Ucma/GRP gene, encoding a new Gla-containing protein. | Experimental cell research 20100115 |
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| Metal-binding affinity and selectivity of nonstandard natural amino acid residues from DFT/CDM calculations. | The journal of physical chemistry. B 20090827 |
| Direct analysis reveals an absence of gamma-carboxyglutamic acid in cancer procoagulant from human tissues. | Blood coagulation & fibrinolysis : an international journal in haemostasis and thrombosis 20090701 |
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| The mineral phase of calcified cartilage: its molecular structure and interface with the organic matrix. | Biophysical journal 20090422 |
| Idiopathic calcinosis cutis. | Indian journal of dermatology 20090101 |
| The PT1-Ca2+ Gla domain binds to a membrane through two dipalmitoylphosphatidylserines. A computational study. | Biochemistry 20081216 |
| Gas6-mediated signaling is dependent on the engagement of its gamma-carboxyglutamic acid domain with phosphatidylserine. | Biochemical and biophysical research communications 20081107 |
| Noninvasive markers of oxidative DNA stress, RNA degradation and protein degradation are differentially correlated with resting metabolic rate and energy intake in children and adolescents. | Pediatric research 20080901 |
| Conantokin-P, an unusual conantokin with a long disulfide loop. | Toxicon : official journal of the International Society on Toxinology 20080801 |
| Proline and gamma-carboxylated glutamate residues in matrix Gla protein are critical for binding of bone morphogenetic protein-4. | Circulation research 20080509 |
| Vitamin K intake and atherosclerosis. | Current opinion in lipidology 20080201 |
| Conorfamide-Sr2, a gamma-carboxyglutamate-containing FMRFamide-related peptide from the venom of Conus spurius with activity in mice and mollusks. | Peptides 20080201 |
| Vascular calcification and uremia: what do we know? | American journal of nephrology 20080101 |
| Detection of a gamma-carboxy-glutamate as novel post-translational modification of human transthyretin. | Protein and peptide letters 20080101 |
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| Post-translational modifications regulate matrix Gla protein function: importance for inhibition of vascular smooth muscle cell calcification. | Journal of thrombosis and haemostasis : JTH 20071201 |
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| [Gas-6 and protein S: vitamin K-dependent factors and ligands for the TAM tyrosine kinase receptors family]. | Medecine sciences : M/S 20071001 |
| Quantum chemical study of the mechanism of action of vitamin K carboxylase (VKC). IV. Intermediates and transition states. | The journal of physical chemistry. A 20070809 |
| Snake-venom-derived Factor IX-binding protein specifically blocks the gamma-carboxyglutamic acid-rich-domain-mediated membrane binding of human Factors IX and X. | The Biochemical journal 20070715 |
| A vasopressin/oxytocin-related conopeptide with gamma-carboxyglutamate at position 8. | The Biochemical journal 20070615 |
| Helix-helix interactions between homo- and heterodimeric gamma-carboxyglutamate-containing conantokin peptides and their derivatives. | The Journal of biological chemistry 20070427 |
| Preferential localization of recombinant factor VIIa to platelets activated with a combination of thrombin and a glycoprotein VI receptor agonist. | Journal of thrombosis and haemostasis : JTH 20070401 |
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| Warfarin-induced vasculopathy. | Journal of thrombosis and thrombolysis 20070201 |
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| Full-length cDNA cloning and protein three-dimensional structure modeling of porcine prothrombin. | Blood cells, molecules & diseases 20070101 |
| Simultaneous generation of aptamers to multiple gamma-carboxyglutamic acid proteins from a focused aptamer library using DeSELEX and convergent selection. | Oligonucleotides 20070101 |
| Growth arrest-specific protein 6 (GAS6) and the protein C pathway. | Critical care (London, England) 20070101 |
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| Molecular dynamics calculations of wild type vs. mutant protein C: relationship between binding affinity to endothelial cell protein C receptor and hereditary disease. | Journal of biomolecular structure & dynamics 20061201 |
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| The role of gamma-carboxylation in the anti-apoptotic function of gas6. | Journal of thrombosis and haemostasis : JTH 20051201 |
| Role of the hexapeptide disulfide loop in the gamma-carboxyglutamic acid domain of protein C in Ca2+-mediated structural and functional properties. | Biochemistry 20050920 |
| Precursors of novel Gla-containing conotoxins contain a carboxy-terminal recognition site that directs gamma-carboxylation. | Biochemistry 20050628 |
| The gamma-carboxyglutamic acid domain of anticoagulant protein S is involved in activated protein C cofactor activity, independently of phospholipid binding. | Blood 20050101 |
| The role of electron capture dissociation in biomolecular analysis. | Mass spectrometry reviews 20050101 |
| Effects of urinary prothrombin fragment 1 in the formation of calcium oxalate calculus. | The Journal of urology 20050101 |
| Structure-function relationships of C-type lectin-related proteins. | Pathophysiology of haemostasis and thrombosis 20050101 |
| Identification of residues Asn89, Ile90, and Val107 of the factor IXa second epidermal growth factor domain that are essential for the assembly of the factor X-activating complex on activated platelets. | The Journal of biological chemistry 20041105 |
| A single amino acid replacement results in the Ca2+-induced self-assembly of a helical conantokin-based peptide. | Biochemistry 20041019 |
| [Serum osteoprotegrin and serum bone gamma-carboxyglutamine acid-containing protein are correlated with bone mineral density in normal women]. | Zhonghua yi xue za zhi 20041002 |
| The first gamma-carboxyglutamic acid-containing contryphan. A selective L-type calcium ion channel blocker isolated from the venom of Conus marmoreus. | The Journal of biological chemistry 20040730 |
| The metal-free and calcium-bound structures of a gamma-carboxyglutamic acid-containing contryphan from Conus marmoreus, glacontryphan-M. | The Journal of biological chemistry 20040730 |
| Isolation and characterization of three novel Gla-containing Conus marmoreus venom peptides, one with a novel cysteine pattern. | Biochemical and biophysical research communications 20040709 |
| Role of the gamma-carboxyglutamic acid domain of activated factor X in the presence of calcium during inhibition by antithrombin-heparin. | Journal of thrombosis and haemostasis : JTH 20040701 |
| Kinetics of factor Xa inhibition by recombinant tick anticoagulant peptide: both active site and exosite interactions are required for a slow- and tight-binding inhibition mechanism. | Biochemistry 20040330 |
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| A new mechanism for metal ion-assisted interchain helix assembly in a naturally occurring peptide mediated by optimally spaced gamma-carboxyglutamic acid residues. | Journal of molecular biology 20040220 |
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| The extended interactions and Gla domain of blood coagulation factor Xa. | Biochemistry 20030708 |
| Crystal structure of Mg2+- and Ca2+-bound Gla domain of factor IX complexed with binding protein. | The Journal of biological chemistry 20030627 |
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| Implication of protein S thrombin-sensitive region with membrane binding via conformational changes in the gamma-carboxyglutamic acid-rich domain. | The Biochemical journal 20011201 |
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