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H-gla-oh

CAS No.:
53861-57-7
Catalog Number:
AG00DBX8
Molecular Formula:
C6H9NO6
Molecular Weight:
191.1388
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
10mg
≥ 99% (TLC)
1 week
United States
$316
- +
50mg
≥ 99% (TLC)
1 week
United States
$798
- +
Product Description
Catalog Number:
AG00DBX8
Chemical Name:
H-gla-oh
CAS Number:
53861-57-7
Molecular Formula:
C6H9NO6
Molecular Weight:
191.1388
MDL Number:
MFCD00011673
IUPAC Name:
(3S)-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)/t3-/m0/s1
InChI Key:
UHBYWPGGCSDKFX-VKHMYHEASA-N
SMILES:
OC(=O)[C@H](CC(C(=O)O)C(=O)O)N
EC Number:
258-825-9
Properties
Complexity:
223  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
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:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-3.7  
Literature
Title Journal
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Critical evaluation of gamma-irradiated serum used as feeder in the culture and demonstration of putative nanobacteria and calcifying nanoparticles. PloS one 20100101
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Carbonic anhydrase I is recognized by an SOD1 antibody upon biotinylation of human spinal cord extracts. International journal of molecular sciences 20100101
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Use of a bacterially expressed human factor IX light chain to develop polyclonal antibody anti-hFIX. Applied biochemistry and biotechnology 20091101
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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
Phylogenetic analysis of ALAD and MGP genes related to lead toxicity. Toxicology and industrial health 20090701
Membrane-dependent interaction of factor Xa and prothrombin with factor Va in the prothrombinase complex. Biochemistry 20090609
From the Gla domain to a novel small-molecule detector of apoptosis. Cell research 20090501
Non-strict strand orientation of the Ca2+-induced dimerization of a conantokin peptide variant with sequence-shifted gamma-carboxyglutamate residues. Peptides 20090501
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Platelet factor 4 impairs the anticoagulant activity of activated protein C. The Journal of biological chemistry 20090227
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Comprehensive analysis of the renal transcriptional response to acute uranyl nitrate exposure. BMC genomics 20060101
Decreased inhibitory activity of prothrombin to calcium oxalate crystallization by specific chemical modification of its gamma-carboxyglutamic acid residues. Urology 20060101
Osteocalcin and bone-specific alkaline phosphatase in sickle cell haemoglobinopathies. Nigerian journal of physiological sciences : official publication of the Physiological Society of Nigeria 20060101
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The role of gamma-carboxylation in the anti-apoptotic function of gas6. Journal of thrombosis and haemostasis : JTH 20051201
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Identification of genes differentially expressed in wild type and Purkinje cell degeneration mice. Molecules and cells 20051031
Role of the hexapeptide disulfide loop in the gamma-carboxyglutamic acid domain of protein C in Ca2+-mediated structural and functional properties. Biochemistry 20050920
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Engineering of a recombinant vitamin K-dependent gamma-carboxylation system with enhanced gamma-carboxyglutamic acid forming capacity: evidence for a functional CXXC redox center in the system. The Journal of biological chemistry 20050318
Rapid fabrication of keratin-hydroxyapatite hybrid sponges toward osteoblast cultivation and differentiation. Biomaterials 20050101
The gamma-carboxyglutamic acid domain of anticoagulant protein S is involved in activated protein C cofactor activity, independently of phospholipid binding. Blood 20050101
Effects of urinary prothrombin fragment 1 in the formation of calcium oxalate calculus. The Journal of urology 20050101
Putative gamma-conotoxins in vermivorous cone snails: the case of Conus delessertii. Peptides 20050101
Vascular ossification-calcification in metabolic syndrome, type 2 diabetes mellitus, chronic kidney disease, and calciphylaxis-calcific uremic arteriolopathy: the emerging role of sodium thiosulfate. Cardiovascular diabetology 20050101
Osteo-Promoter Database (OPD) -- promoter analysis in skeletal cells. BMC genomics 20050101
Expression profiling of laser-microdissected intrapulmonary arteries in hypoxia-induced pulmonary hypertension. Respiratory research 20050101
Structure-function relationships of C-type lectin-related proteins. Pathophysiology of haemostasis and thrombosis 20050101
Chemical modification of cysteine residues is a misleading indicator of their status as active site residues in the vitamin K-dependent gamma-glutamyl carboxylation reaction. The Journal of biological chemistry 20041224
Conantokins: peptide antagonists of NMDA receptors. Current medicinal chemistry 20041201
Total chemical synthesis and NMR characterization of the glycopeptide tx5a, a heavily post-translationally modified conotoxin, reveals that the glycan structure is alpha-D-Gal-(1-->3)-alpha-D-GalNAc. European journal of biochemistry 20041201
Oral anticoagulant treatment: friend or foe in cardiovascular disease? Blood 20041115
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
Processing and transport of matrix gamma-carboxyglutamic acid protein and bone morphogenetic protein-2 in cultured human vascular smooth muscle cells: evidence for an uptake mechanism for serum fetuin. The Journal of biological chemistry 20041008
[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
Multiple 6-bromotryptophan residues in a sleep-inducing peptide. Biochemistry 20040928
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
Vitamin K-dependent Gas6 activates ERK kinase and stimulates growth of cardiac fibroblasts. Biochemical and biophysical research communications 20040702
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
Matrix GLA protein modulates branching morphogenesis in fetal rat lung. American journal of physiology. Lung cellular and molecular physiology 20040601
Platelet factor 4 modulation of the thrombomodulin-protein C system. Critical care medicine 20040501
Determining sequences and post-translational modifications of novel conotoxins in Conus victoriae using cDNA sequencing and mass spectrometry. Journal of mass spectrometry : JMS 20040501
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
Effects of vitamin K2 in hemodialysis patients with low serum parathyroid hormone levels. Bone 20040301
Binding of the factor IX gamma-carboxyglutamic acid domain to the vitamin K-dependent gamma-glutamyl carboxylase active site induces an allosteric effect that may ensure processive carboxylation and regulate the release of carboxylated product. The Journal of biological chemistry 20040220
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
[Effect of raloxifene hydrochloride on bone mineral density, bone metabolism and serum lipids in Chinese postmenopausal women with osteoporosis]. Zhonghua yi xue za zhi 20040217
Beneficial effects of vitamins D and K on the elastic properties of the vessel wall in postmenopausal women: a follow-up study. Thrombosis and haemostasis 20040201
Use of snake venom inhibitors in studies of the function and tertiary structure of coagulation factors. International journal of hematology 20040201
Effects of vitamin K2 on osteoporosis. Current pharmaceutical design 20040101
The tissue factor/factor VIIa/factor Xa complex: a model built by docking and site-directed mutagenesis. Proteins 20031115
Determination of disulfide bond assignment of human vitamin K-dependent gamma-glutamyl carboxylase by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. The Journal of biological chemistry 20031114
[Study on association of polymorphism of MGP(T-138C) gene and blood lead level in children]. Wei sheng yan jiu = Journal of hygiene research 20031101
Vitamin K and bone health. The Proceedings of the Nutrition Society 20031101
Potentiating effect of distant sites in non-phosphorylated cyclic peptide antagonists of the Grb2-SH2 domain. Biochemical and biophysical research communications 20031017
Glucocorticoid effects on vitamin K-dependent carboxylase activity and matrix Gla protein expression in rat lung. American journal of physiology. Lung cellular and molecular physiology 20030901
Structural basis of membrane binding by Gla domains of vitamin K-dependent proteins. Nature structural biology 20030901
The Gla domain of factor IXa binds to factor VIIIa in the tenase complex. The Journal of biological chemistry 20030815
The extended interactions and Gla domain of blood coagulation factor Xa. Biochemistry 20030708
Intracrystalline proteins and urolithiasis: a synchrotron X-ray diffraction study of calcium oxalate monohydrate. Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research 20030701
Crystal structure of Mg2+- and Ca2+-bound Gla domain of factor IX complexed with binding protein. The Journal of biological chemistry 20030627
Diagnostic value of protein induced by vitamin K absence (PIVKAII) and hepatoma-specific band of serum gamma-glutamyl transferase (GGTII) as hepatocellular carcinoma markers complementary to alpha-fetoprotein. British journal of cancer 20030616
Direct binding properties of conantokins to native N-methyl-d-aspartate receptors. The journal of peptide research : official journal of the American Peptide Society 20030601
Site-directed fluorescence probing to dissect the calcium-dependent association between soluble tissue factor and factor VIIa domains. Biochimica et biophysica acta 20030530
Role of the Gla and first epidermal growth factor-like domains of factor X in the prothrombinase and tissue factor-factor VIIa complexes. The Journal of biological chemistry 20030321
Gla domain-mutated human protein C exhibiting enhanced anticoagulant activity and increased phospholipid binding. Blood 20030315
The factor IX gamma-carboxyglutamic acid (Gla) domain is involved in interactions between factor IX and factor XIa. The Journal of biological chemistry 20030307
Mutagenesis of the gamma-carboxyglutamic acid domain of human factor VII to generate maximum enhancement of the membrane contact site. The Journal of biological chemistry 20030307
Deletion or replacement of the second EGF-like domain of protein S results in loss of APC cofactor activity. Blood 20030215
Cloning and expression of rat coagulation factor VII. Thrombosis research 20030215
Isolation, structure, and activity of GID, a novel alpha 4/7-conotoxin with an extended N-terminal sequence. The Journal of biological chemistry 20030131
Identification of a gene encoding a typical gamma-carboxyglutamic acid domain in the tunicate Halocynthia roretzi. Journal of thrombosis and haemostasis : JTH 20030101
Expression and characterization of recombinant vitamin K-dependent gamma-glutamyl carboxylase from an invertebrate, Conus textile. European journal of biochemistry 20021201
Structure of a novel P-superfamily spasmodic conotoxin reveals an inhibitory cystine knot motif. The Journal of biological chemistry 20021108
Chronic disseminated intravascular coagulation and childhood-onset skin necrosis resulting from homozygosity for a protein C Gla domain mutation, Arg15Trp. Journal of pediatric hematology/oncology 20021101
Gas6 binding to photoreceptor outer segments requires gamma-carboxyglutamic acid (Gla) and Ca(2+) and is required for OS phagocytosis by RPE cells in vitro. Experimental eye research 20021001
Vitamin K-dependent protein S localizing complement regulator C4b-binding protein to the surface of apoptotic cells. Journal of immunology (Baltimore, Md. : 1950) 20020901
High-performance liquid chromatography--mass spectrometry and electron-capture dissociation tandem mass spectrometry of osteocalcin. Determination of gamma-carboxyglutamic acid residues. Journal of chromatography. A 20020712
Circulating and binding characteristics of wild-type factor IX and certain Gla domain mutants in vivo. Blood 20020701
Growth characteristics, angiotensin II generation, and microarray-determined gene expression in vascular smooth muscle cells from young spontaneously hypertensive rats. Journal of hypertension 20020701
Characteristics and composition of the vitamin K-dependent gamma-glutamyl carboxylase-binding domain on osteocalcin. The Biochemical journal 20020515
gamma-Carboxyglutamic acid content of hepatocellular carcinoma-associated des-gamma-carboxy prothrombin. Biochimica et biophysica acta 20020424
Detection of vitamin K-dependent proteins in venoms with a monoclonal antibody specific for gamma-carboxyglutamic acid. Toxicon : official journal of the International Society on Toxinology 20020401
Effect of prothrombin and its activation fragments on calcium oxalate crystal growth and aggregation in undiluted human urine in vitro: relationship between protein structure and inhibitory activity. Clinical science (London, England : 1979) 20020401
Structure and dynamics of zymogen human blood coagulation factor X. Biophysical journal 20020301
A human antibody that inhibits factor IX/IXa function potently inhibits arterial thrombosis without increasing bleeding. Arteriosclerosis, thrombosis, and vascular biology 20020301
Discovery of a high molecular weight complex of calcium, phosphate, fetuin, and matrix gamma-carboxyglutamic acid protein in the serum of etidronate-treated rats. The Journal of biological chemistry 20020208
Localization of phosphatidylserine binding sites to structural domains of factor Xa. The Journal of biological chemistry 20020118
Ca2+ binding to proteins containing gamma-carboxyglutamic acid residues. Methods in molecular biology (Clifton, N.J.) 20020101
Effects of skeletal loading on bone mass and compensation mechanism in bone: a new insight into the 'mechanostat' theory. Journal of bone and mineral metabolism 20020101
Identification of extrinsic blood coagulation pathway inhibitors from the tick Ornithodoros savignyi (Acari: Argasidae). Experimental parasitology 20020101
Implication of protein S thrombin-sensitive region with membrane binding via conformational changes in the gamma-carboxyglutamic acid-rich domain. The Biochemical journal 20011201
Fourier-transform infrared spectroscopic study of Ca2+-binding to osteocalcin. Calcified tissue international 20011201
A novel fluorescence assay to study propeptide interaction with gamma-glutamyl carboxylase. Biochemistry 20011002
Matrix gamma-carboxyglutamic acid protein is a key regulator of PTH-mediated inhibition of mineralization in MC3T3-E1 osteoblast-like cells. Endocrinology 20011001
Spin and fluorescent probing of the binding interface between tissue factor and factor VIIa at multiple sites. Biophysical journal 20011001
An anti-EGF monoclonal antibody that detects intramolecular communication in factor IX. Biochemical and biophysical research communications 20010907
Functional mapping of anti-factor IX inhibitors developed in patients with severe hemophilia B. Blood 20010901
Structure-function relationships of the NMDA receptor antagonist conantokin peptides. Current drug targets 20010901
A polymorphism of the human matrix gamma-carboxyglutamic acid protein promoter alters binding of an activating protein-1 complex and is associated with altered transcription and serum levels. The Journal of biological chemistry 20010831
A comparative study of the adsorption of amino acids on to calcium minerals found in renal calculi. Clinical science (London, England : 1979) 20010801
Expression and localization of MGP in rat tooth cementum. Archives of oral biology 20010701
The omega-loop region of the human prothrombin gamma-carboxyglutamic acid domain penetrates anionic phospholipid membranes. The Journal of biological chemistry 20010629
Functional preference of the constituent amino acid residues in a phage-library-based nonphosphorylated inhibitor of the Grb2-SH2 domain. The journal of peptide research : official journal of the American Peptide Society 20010601
Induction of acquired factor IX inhibitors in cynomolgus monkey (Macaca fascicularis): a new primate model of hemophilia B. Thrombosis research 20010515
Synthesis of gamma-carboxylated polypeptides by alpha-cells of the pancreatic islets. Biochemical and biophysical research communications 20010504
Amino acid determinants for NMDA receptor inhibition by conantokin-T. Journal of neurochemistry 20010501
Combined deficiency of factors II, VII, IX, and X (Borgschulte-Grigsby deficiency) in pregnancy. Obstetrics and gynecology 20010501
Total chemical synthesis of human matrix Gla protein. Protein science : a publication of the Protein Society 20010401
On a potential global role for vitamin K-dependent gamma-carboxylation in animal systems. Evidence for a gamma-glutamyl carboxylase in Drosophila. The Journal of biological chemistry 20010316
Sequence requirements for the N-methyl-D-aspartate receptor antagonist activity of conantokin-R. The Journal of biological chemistry 20010309
Posttranslational modifications of recombinant myotube-synthesized human factor IX. Blood 20010101
Novel vitamin K-dependent pathways regulating cell survival. Apoptosis : an international journal on programmed cell death 20010101
1,25-Dihydroxyvitamin D3 promotes vitamin K2 metabolism in human osteoblasts. Osteoporosis international : a journal established as result of cooperation between the European Foundation for Osteoporosis and the National Osteoporosis Foundation of the USA 20010101
Articular cartilage and changes in arthritis: noncollagenous proteins and proteoglycans in the extracellular matrix of cartilage. Arthritis research 20010101
Comparative effect of L-CCG-I, DCG-IV and gamma-carboxy-L-glutamate on all cloned metabotropic glutamate receptor subtypes. Neuropharmacology 19980801
Propeptide and glutamate-containing substrates bound to the vitamin K-dependent carboxylase convert its vitamin K epoxidase function from an inactive to an active state. Proceedings of the National Academy of Sciences of the United States of America 19970819
Carboxyl-terminal proteolytic processing of matrix Gla protein. The Journal of biological chemistry 19911105
Synthesis of a gamma-carboxyglutamic acid containing heptapeptide corresponding to bovine prothrombin residues 17-23. International journal of peptide and protein research 19861201
Gamma-carboxyglutamate in a neuroactive toxin. The Journal of biological chemistry 19841210
Vitamin K dependent carboxylation: synthesis and biological properties of tetrazolyl analogues of pentapeptidic substrates. Journal of medicinal chemistry 19840901
Vitamin K dependent carboxylation of glutamate residues to gamma-carboxyglutamate in microsomes from spleen and testes: comparison with liver, lung, and kidney. Biochemistry 19830301
Vitamin K-dependent carboxylase: synthesis of an inhibitor of the glutamyl binding site. FEBS letters 19830207
Mechanism of action of vitamin K: synthesis of gamma-carboxyglutamic acid. CRC critical reviews in biochemistry 19800101
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