Y-carboxyglutamic acid

Hydroxylated amino acids (eg, 4-hydroxyproline, 5-hydroxylysine) and A/-methylated amino acids (eg, /V-methylhistidine) are obtained by the acid hydrolysis of proteins. y-Carboxyglutamic acid occurs as a component of some sections of protein molecules it decarboxylates spontaneously to L-glutamate at low pH. These examples are formed upon the nontranslational modification of protein and are often called secondary protein amino acids... 

Aminoadipic acid y-Carboxyglutamic acid Pyroglutatnic acid Phosphoserine Phospho threonine Phospho tyrosine... 

C2 domains, 46 460-465 y-carboxyglutamic acid sites, 46 465 70 Calcium nitrate, preparation of, 6 125 Calcium pentaphosphate, 4 37-38 Calcium phthalocyanine, preparation of, 7 ... 

Czerwiec E, Kalume DE, Roepstorff P, Hambe B, Furie B, Furie BC, Stenflo J (2006) Novel y-Carboxyglutamic Acid-Containing Peptides from the Venom of Conus textile. FEBS J 273 2779... 

N. L. Kelleher, R. A. Zubarev, K. Bush, B. Furie, B. C. Furie, F. W. McLafferty, and C. T. Walsh, Localization of labile posttranslational modifications by electron capture dissociation The case of y-carboxyglutamic acid, Anal. Chem., 71 (1999) 4250 1253. 

SpA, Staphylococcal protein A PpL, protein L from Peptostreptococcus Magnus IgG, immunoglobulin G Gla, y-carboxyglutamic acid SPR, surface plasmon resonance ELISA, enzyme-linked immunosorbent assay FITC, fluorescein isothiocyanate NMR, nuclear magnetic resonance... 

The majority of conotoxin structures (115 of 125 structures in the PDB) have been determined by NMR spectroscopy as opposed to X-ray crystallography. They have significant structural diversity as a result of their diverse sequences and disulphide connectivities. Furthermore, conotoxins also have a large number of post-translational modifications, including the presence of hydroxyproline, y-carboxyglutamic acid and bromotryptophan residues, epimerisation, glycosyla-tion and amidation,144,145 that enhance their structural diversity. A recent analysis of NMR data for the unusual amino acids present in conotoxins3 provides a reference source for chemical shifts of post-translationally modified amino acids. 

Widespread e.g. Vaccinium corymbosum (Ericaceae), Medicago saliva (alfalfa) (Fabaceae), Castaneasp. (chestnut) (Fagaceae) [leaf]), Triticum aestivum (Poaceae) Dihydro form (KH ) coenzyme for "y-carboxyglutamic acid formation on procoagulant factors II, VII, IX X, anticoagulant proteins C S, matrix Gla protein osteocalcin... 

Intestinal bacteria dihydro form (KH9) coenzyme for "y-carboxyglutamic acid formation on procagulant factors II, VII, IX X, anticoagulant proteins C S, matrix Gla protein osteocalcin... 

The Mannich bases investigated are acctoacetic and malonic acid derivatives, Y-carboxyglutamic acid included. - Compounds having the lactone structure give preferably decarboxylation of the ester groups not involved in the lactone ring. - ... 

Boggs, N. T., Chemical modification of peptides containing y-carboxyglutamic acid, J. Org. Chem., 47, 1812. 1982. 

Carboxylation. Bredereck s reagent has been used in a simple synthesis of L-y-carboxyglutamic acid (S), an unusual natural amino add present in prothrombin and believed to be involved in elotting. The starting material is the lactam 1 derived from L-glutamic acid and available commercially. It is converted by reaction with this reagent into the enamide 2. Reaction with 2,2,2-trichloroethoxycarbonyl chloride transforms 2 into the trichloroethyl ester 3 in moderate yield. The synthesis of 5 is completed by reaction with benzyl alcohol and triethylamine followed by hy drogenolysis. ... 

A very recent paper by Robertson etal. l 08) explores the utilization of NMR for the study of Mg binding to y-carboxyglutamic acid-containing peptides. These are taken as a model for prothrombin, an enzyme possessing 10 y-carboxyglutamic acid residues and which is known to interact with Mg and Ca. Whereas the addition of the peptide to an aqueous solution of Mg affects the line-width rather than the shift, the Ca line-widths remain almost invariant in the... 

Z = benzyloxycarbonyl, Gla = y-carboxyglutamic acid) relative to an arbitrary standard in H2O at pH 6-6. Initial calcium concentration was 19-5mM. (108)... 

Hamilton S. E., et al. (1982) y-carboxyglutamic acid in invertebrates its identification in hermatypic corals. Bio-chem. Biophys. Res. Commun. 108, 610-613. 

Sokoll, L., Booth, S., O Brien, M., Davidson, K. W.,Tsaioun, K. I.,and Sadowski, J. A. (1997). Changes in serunt osteocalcin, plasma phylloquinone, and urinary y-carboxyglutamic acid in response to altered intakes of dietary phylloquinone in human subjects. Am. J. CJin.. iVHlr. 65, 779-784. 

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