3-Amino-4-hydroxypropionic acid

Prien et al. [18] used secondary amines for the formation of 1,3-amino alcohols. Another substituent was introduced by aminolytic cleavage under the formation of C(2), C(3)-disubstituted 3-hydroxypropionic acid amides. Thirty-six compounds were synthesized, with yields ranging from 40 % to 66 % (Fig. 6.6). 

L-serine (S)-(-)-serine Ser S L-2-amino-3-hydroxypropionic acid L-(-)-serine 2-amino-3-hydroxypropionic acid 3-hydroxyalanine. Naturally xcurring enantiomer of serine. Used in bixhemical research, as a dietary supplement, in culture media, microbiological tests, feed additive, mp = 228 (dec) [a]8°= -7 (c = 10.41 H2O) soluble in H2O, insoluble in organic solvents. Degussa AG Janssen Chimica Mitsui Toatsu Nippon Rikagakuyakuhin U.S. BioChem. 

CAS 312-84-5 EINECS/ELINCS 206-229-4 Synonyms D-2-Amino-3-hydroxypropanoic acid (R)-2-Amino-3-hydroxypropionic acid D-(+)-serine... 

CAS 302-84-1 EINECS/ELINCS 206-130-6 Synonyms (+-2)-Amino-3-hydroxypropionic acid... 

CAS 56-45-1 EINECS/ELINCS 200-274-3 Synonyms 2-Amino-3-hydroxypropionic acid L-P-Hydroxyalanine Ser Serine (INCI) (S)-(+)-Serine... 

Glycine (2-aminoacetic acid), L-serine [(S)-2-amino-3-hydroxypropionic acid] and L-alanine [(S)-2-aminopropionic acid] are simple -amino acids. The secondary products derived... 

A mixture of 8.5 g. a,a-diphenyl- -hydroxypropionic acid hydrazide, LiAlH4, and ethylmorpholine heated 4 hrs. at 100° 5.1 g. y-amino-/ ,j5-diphenylpro-... 

Examination of plasma and urine revealed elevated quantities of jff-ala-nine, 3-hydroxypropionic acid, (R)- and (S)-3-aminoisobutyric acid, (R)-and (S)-3-hydroxyisobutyric acid and (S)-2-hydroxymethylbutyric acid. Direct enzymatic assay of methylmalonate semialdehyde dehydrogenase is unavailable revealed homozygosity for DNA analysis 1336 G>A transversion which substituted an arginine for a highly conserved glycine at amino acid residue 446. 

Warnecke, T.E., Lynch, M.D., Lipscomb, M.L., and Gill, R.T. (2012) Identification of a 21 amino acid peptide conferring 3-hydroxypropionic acid stress-tolerance to Escherichia coli. Biotechnol. Bioeng, 109 (5), 1347-1352. 

Microbial or enzymatic conversion of renewable resources Lactic acid Succinic acid 1.3- Propanediol Itaconic acid 2.3- Butanediol 3-Amino-4-hydroxy- benzoic acid Amino acids Glucose Trehalose Glucaric acid Erythritol P-Hydroxybutyric acid P-Hydroxypropionic acid Itaconic acid Isoprene ... 

Serine (a-amino- 3-hydroxypropionic acid) contains an alcoholic hydroxyl group which may engage in the usual reactions, such as ester formation. Esters with phosphoric acid have physiological significance as components of nucleotides and some proteins. The unesterified serine residue appears to possess special functions in several enzymes. 

THF (13.5 ml) and DMF (1.5 ml) are cooled to -35°C and degased by alternating reduced pressure and nitrogen three times. Thiophenol (0.22 ml, 2.14 mmol) is added followed by potassium butoxide/THF (1.978 M, 0.7 ml, 1.38 mmol). After 5 min, 7-SDMS baccatin III 13-(2R,4S,5R)- and (2S,4S,5R)-2,4-diphenyl-3-(4-nitrobenzenesulfonamido)-l,3-oxazolidine-5-carboxylic acid ester (877 mg, 0.762 mmol) is added. After the solids are added, the reaction mixture is slowly warmed to -10°C. The mixture is stirred at -10°C until the red color fades to yellow. After 3 h the bath is dropped allowing the mixture to warm to 20-25°C. At 20°-25°C the reaction is stirred for 1 h before assaying by TLC and HPLC. Sodium bisulfite (241 mg, 2.31 mmol) is added in water (5 ml). The mixture is stirred at 20°-25°C and after approximately 115 h the reaction is complete (by TLC) giving the free amine 7-SDMS baccatin III 13-(2R,3S)-3-amino-3-phenyl-2-hydroxypropionate. 

Lantibiotics contain several unusual amino acids, including the thioether lanthionine (Lan) hnkage and its methyl substituted analog methyUanthionine (MeLan) (Fig. la) that unifies all members of the class and accounts for their family name. In addition to Lan, lantibiotics commonly contain 2,3-dehydroalanine (Dha) and (Z)-2,3-dehydrobutyrine (Dhb). In all, no less than 15 different posttranslational modifications have been documented in lantibiotics (for a selection see Fig. la), and up to 58% of their amino acids are modified. These extensive structmal alterations overcome the constraints imposed by the use of 20 amino acids in ribosomally synthesized peptides. Some less common, posttranslationally crafted residues in lantibiotics are fS-hydroxy aspartate, lysinoalanine, aminovinyl cysteine (AviCys), D-alanine, 2-oxobutyrate, 2-oxopropionate, and 2-hydroxypropionate. The presence of these unusual residues is thought to be important for the biological activity of lantibiotics. 

Bupropion hydroxylation of the tert-butyl group to hydroxypropion is mediated almost exclusively by CYP2B6 and, to a lesser extent, by CYP2E1 (74). Other metabolites include reduction of the aminoketone to amino-alcohol isomers, threo-hydrobupropion and erythro-hydrobupropion (Fig. 21.21). Further oxidation of the bupropion side chain results in the formation of m-chlorobenzoic acid, which is eliminated in the urine as its glycine conjugate. Hydroxybupropion is approximately 50% as potent as bupropion, whereas threo-hydrobupropion and erythro-hydrobupropion have 20% of the potency of bupropion. Peak plasma concentrations for hydroxybupropion are approximately 10 times the peak level of the parent drug at steady state, with an elimination half-life of approximately 20 hours. The times to... 

Methyl 3-(2-Pyridyl)amino-2-hydroxypropionate heated at 150° 2,3-dihydro-imidazo[l,2-a]pyridine-3-carboxylic acid betaine. Y 72%. F. e. and multi-step procedure s. P. Reynaud, J. Mandereau, and R. Moreau, G. r. 251, 2992 (1960). 

Acute episodes are characterized by massive ketonuria. Amino acid analysis reveals large amounts of glycine in plasma and urine. The diagnosis is best made by organic acid analysis of the urine. The key compounds are methylcitrate and 3-hydroxypropionate. GCMS analysis for methylcitrate provides for a rapid and specific approach to prenatal diagnosis. 

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