Amino acids Ammonium

Amino acids, ammonium, peptides Sulfate, (sulfite)... 

Henry, H. A. L., and Jefferies, R. L. (2002). Free amino acid, ammonium and nitrate concentrations in soil solutions of a grazed coastal marsh in relation to plant growth. Plant Cell Environ. 25, 665-675. 

Istre O, Jellum E, Skajaa K, Forman A. Changes in amino acids, ammonium, and coagulation factors after transcervical resection of the endometrium with a glycine solution used for uterine irrigation. Am J Obstet Gynecol 1995 172(3) 939M5. 

Detellier. C. Laszlo. P. Influence of amino acids, ammonium and potassium cations on the self-assembly of 5 -GMP. Helv. Chim. Acta 1979, 62. 1559-1565. 

Alanine glutamate Aldioxa Aleuritic acid Aluminum capryloyl hydrolyzed collagen Aluminum undecylenoyl collagen amino acids Ammonium dimethicone copolyol sulfate Ammonium glycyrrhizate Ammonium hydrolyzed collagen Amniotic fluid AMP-isostearoyl gelatin/keratin amino acids/lysine hydroxypropyltrimonium chloride AMP-isostearoyl hydrolyzed soy protein AMP isostearoyl hydrolyzed wheat protein Amyl... 

Aluminium hydroxide Aluminium salts Amino acids Ammonium chloride n-Butanol Benzoic acid Benzyl alcohol Betaine... 

The above method of preparing a neutral solution of the ammonium salt cannot be applied to extremely weak acids (e.g., some amino-acids), the ammonium salts of which dissociate in boiling aqueous solution. 

Amino acids may be prepared by the action of a large excess of concentrated ammonia solution upon a-chloro- or a-bromo-acids the presence of a considerable amount of ammonium carbonate often increases the yield of monoamino acid, for example ... 

Place 425 ml. of concentrated ammonia solution (sp. gr. 0-88) in a 500 ml. round-bottomed flask and add slowly 75 g. of a-bromocaproic acid (Section 111,126). Stopper the flask tightly and allow it to stand in a warm place (50-55°) for 30 hours. Filter the amino acid at the pump and keep the filtrate A) separately. Wash the amino acid (ca. 26 g.) well with methyl alcohol to remove the ammonium bromide present. Evaporate the aqueous filtrate (A) almost to dryness on a steam bath. 

Miscellaneous Reactions. Sodium bisulfite adds to acetaldehyde to form a white crystalline addition compound, insoluble in ethyl alcohol and ether. This bisulfite addition compound is frequendy used to isolate and purify acetaldehyde, which may be regenerated with dilute acid. Hydrocyanic acid adds to acetaldehyde in the presence of an alkaU catalyst to form cyanohydrin the cyanohydrin may also be prepared from sodium cyanide and the bisulfite addition compound. Acrylonittile [107-13-1] (qv) can be made from acetaldehyde and hydrocyanic acid by heating the cyanohydrin that is formed to 600—700°C (77). Alanine [302-72-7] can be prepared by the reaction of an ammonium salt and an alkaU metal cyanide with acetaldehyde this is a general method for the preparation of a-amino acids called the Strecker amino acids synthesis. Grignard reagents add readily to acetaldehyde, the final product being a secondary alcohol. Thioacetaldehyde [2765-04-0] is formed by reaction of acetaldehyde with hydrogen sulfide thioacetaldehyde polymerizes readily to the trimer. 

Synthesis from Aldehydes and Ketones. Treatment of aldehydes and ketones with potassium cyanide and ammonium carbonate gives hydantoias ia a oae-pot procedure (Bucherer-Bergs reactioa) that proceeds through a complex mechanism (69). Some derivatives, like oximes, semicarbazones, thiosemicarbazones, and others, are also suitable startiag materials. The Bucherer-Bergs and Read hydantoia syntheses give epimeric products when appHed to cycloalkanones, which is of importance ia the stereoselective syathesis of amino acids (69,70). 

Polypeptide Synthesis and Analysis. Sihca or controUed-pore glass supports treated with (chloromethyl)phenylethyltrimethoxysilane [68128-25-6] or its derivatives are replacing chloromethylated styrene—divinylbenzene (Merrifield resin) as supports in polypeptide synthesis. The sdylated support reacts with the triethyl ammonium salt of a protected amino acid. Once the initial amino acid residue has been coupled to the support, a variety of peptide synthesis methods can be used (34). At the completion of synthesis, the anchored peptide is separated from the support with hydrogen bromide in acetic acid (see Protein engineering Proteins). 

Urea (24), amino acids (25), and creatinine (26) are also decomposed during superchlorination or shock treatment, with formation of N2 and other oxidation products. However, the process is slower than with ammonium ion (see Chloramines and BROMAMINEs). Urea is the principal nitrogen-containing compound in swimming pools. Since it is an amide, it reacts slowly with chlorine, yielding N2, NCl, and NO/ (27). 

The mixture of D and L optical forms of this hydroxy analogue of methionine is converted to the calcium salt which is used in animal feed supplements. Cyanohydrins react with ammonium carbonate to form hydantoins (2), which yield amino acids upon hydrolysis. Commercial DL-methionine [59-57-8] is produced by hydrolysis of the hydantoin of 3-meth5ithiopropionaldehyde [3268-49-3]. 

Hydroxyl Group. The OH group of cyanohydrins is subject to displacement with other electronegative groups. Cyanohydrins react with ammonia to yield amino nitriles. This is a step in the Strecker synthesis of amino acids. A one-step synthesis of a-amino acids involves treatment of cyanohydrins with ammonia and ammonium carbonate under pressure. Thus acetone cyanohydrin, when heated at 160°C with ammonia and ammonium carbonate for 6 h, gives a-aminoisobutyric acid [62-57-7] in 86% yield (7). Primary and secondary amines can also be used to displace the hydroxyl group to obtain A/-substituted and Ai,A/-disubstituted a-amino nitriles. The Strecker synthesis can also be appHed to aromatic ketones. Similarly, hydrazine reacts with two molecules of cyanohydrin to give the disubstituted hydrazine. 

In 1959 a new non-protein L-a-amino acid was isolated from the seeds of Acacia willardiana and later from other species of Acacia-, it proved to be l-/3-amino-/3-carboxyethyluracil (977) (59ZPC(316)164). The structure was confirmed by at least four syntheses in the next few years. The most important involves a Shaw synthesis (Section 2.13.3.1.2e) of the acetal (975) and hydrolysis to the aldyhyde (976) followed by a Strecker reaction (potassium cyanide, ammonia and ammonium chloride) to give DL-willardiine (977) after resolution, the L-isomer was identical with natural material (62JCS583). Although not unambiguous, a Principal Synthesis from the ureido acid (978) and ethyl formylacetate is the most direct route (64ZOB407). 

The effect of pH is rarely of use for pK measurement it is more often of use in identifying the site of protonation/deprotonation when several basic or acidic sites are present. Knowing the incremental substitutent effects Z of amino and ammonium groups on benzene ring shifts in aniline and in the anilinium ion (40), one can decide which of the nitrogen atoms is protonated in procaine hydrochloride (problem 24). 

The reagent neutralizes the sulfuric acid and decomposes the ammonium sulfate, but it does not react with the amino acid. 

The amino acid and the ammonium chloride may conveniently be separated by passing through a column of ion-exchange resins. The amino acid melts at 195°C. 

Assimilatory nitrate reduction Conversion of nitrate to reduced forms of nitrogen, generally ammonium, for the synthesis of amino acids and proteins. 

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