Acetic guanidino

FIGURE 8.14 Salts of amino acids. (A) Acetic acid and aqueous ammonia form salts with the basic and acidic amino acids but (B) not with neutral amino acids. (C) Stronger acids and bases form salts with all amino, guanidino and carboxyl groups of amino acids. Ac = acetyl R = alkyl or cyclohexyl. 

Creatine does not derive from the muscles themselves, but is synthesized in two steps in the kidneys and liver (left part of the illustration). Initially, the guanidino group of arginine is transferred to glycine in the kidneys, yielding guanidino acetate [3]. In the liver, N-methylation of guanidino acetate leads to the formation of creatine from this [4]. The coenzyme in this reaction is S-adenosyl methionine (SAM see p. 110). 

Special assays (urine and plasma) lactate, orotidine, thiosulphate, carnitine, succinylacetone, hydroxyproline, urate, orotate, sialic acid, MPS, guanidino-acetate, HVA, pyroglutamate, 5H1AA, pipecolate, pyruvate, 3-hydroxybutyrate, phytanate, VLCFA, homocysteine, 7-dehydrocholesterol, phenylalanine ERNDIM 8 148... 

Fig. 7.2.2 Derivatisation scheme for GA and Cr. R = CH3 creatine, R = H guanidino acetate, RT room temperature...

Table 7.2.1 Calibration curves for guanidino acetate (GA). CSF Cerebrospinal fluid, IS internal standards...

Acetamido-2,6-anhydro-3,4,5-trideoxy-4-guanidino-D-glycero-D-galacto-non-2-enonic acid Sodium acetate Cyanogen bromide Hydrazine... 

Compound 10b has been treated with a solution of the nitrating mixture made from acetic anhydride and nitric acid in dioxane affording nitro derivative 10c, with not very high yields. The catalytic reduction of nitro derivative 10c, carried out with hydrazine in ethanol in the presence of palladium on calcium carbonate, affords compound lOd. The guanidino group at C-5 has be i introduced by reaction of compound lOd with ( anamide in solution of hydrochloric acid affording the objective molecule 10. 

Nofre, C., Tinti, J.-M., Chatzopoulos-Ouar, F. Preparation of (phenyl-guanidino)- and [[(l-phenylamino)ethyl]amino]acetic acids as sweeteners. Eur. Pat. Appl. EP 241,395 Chem. Abtr 1988,109. 190047k 1987. 

Strongly basic cationic phosphine ligands 75, 76 containing guanidino functions were prepared either in the reaction of 3-aminopropyldiphenylphosphine with lH-pyrazole-l-carboxamide under basic conditions in DMF [75] or by the addition of dimethylcyanamide to the amino groups of tertiary (3-aminophenyl)phosphines in acidic medium [70], These phosphines (as acetate or chloride salts) are highly soluble in water in some cases the solubility reaches that of TPPMS. Another noteworthy feature of these compounds that they are considerably less sensitive to air oxidation then the anionic (e.g. sulfonated) phosphines. 

Glyceryl guaiacolate Glycine anhydride Guanethidine sulfate Guanidino acetic acid... 

Free peptides can be examined by paper electrophoresis or by thin layer electrophoresis as well. If one or more cation forming groups, (amino group, guanidino group, imidazole) are present, electrophoresis in an acidic solvent, such as dilute acetic acid, is most revealing. Compounds with free carboxyl groups are best run under basic conditions to allow differentiation by the number of carboxylate anions. The acidic character of the phenolic hydroxyl in tyrosine should be included in these considerations. 

Guanidino compounds can be readily cyclized by reaction with malondialdehyde, either as such or in the form of its diethyl acetal, 1,1,3,3-tetraethoxypropane, giving substituted pyrimidines, which may have improved chromatographic properties increased detectability (UV absorption after TLC) and potentially also increased volatility for analysis by GC [93,94],... 

Synthetic details have now been given for the important guanidino-derivadve 55, a potent inhibitor of influenza virus sialidase, and the 4-deoxycompound 56 has been made by elimination of acetic acid fiom a known intermediate (Vol. 25, p. 188) the truncated analogue 57 was also reported, made by a similar synthesis (C5 + C2) from di-O-isopropylidene-u/de ydo-L-arabinose. The 3-ene 58 has also been prepared from iV-acetylmannosamine. A route to reduced derivatives of NeuNAc by chain extension is mentioned in Chapter 2. 

Bodamer OA, Bloesch SH, Stockler-Ipsiroglu S, O Brien WE. Analysis of guanidino-acetate and creatine by isotope dilution electrospray tandem mass-spectrometry. Clin Chim Acta 2001 308 173-178... 

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