454-28-4Relevant articles and documents
Facile synthesis of optically active homocysteine from methionine
Shiraiwa, Tadashi,Nakagawa, Kazuo,Kanemoto, Norito
, p. 468 - 469 (2000)
L-Methionine (L-Met) reacted with dichloroacetic acid in concentrated hydrochloric acid under refluxing to give (45)-1,3-thiazane-2,4-dicarboxylic acid hydrochloride [(4S)-TDC· HCl]. L-Homocysteine (L-Hcy) was obtained in an optically pure form by treatme
A green and expedient synthesis of enantiopure diketopiperazines via enzymatic resolution of unnatural amino acids
Pereira, Pedro C.,Arends, Isabel W.C.E.,Sheldon, Roger A.
supporting information, p. 4991 - 4993 (2015/01/09)
Dipeptides comprising a d-phenylglycyl moiety coupled to the l-enantiomer of 2-amino butyric acid, norvaline, norleucine, and homocysteine were successfully synthesized from d-phenylglycine amide and the racemate of the corresponding unnatural amino acid.
Synthesis of optically active homocysteine from methionine and its use in preparing four stereoisomers of cystathionine
Shiraiwa, Tadashi,Nakagawa, Kazuo,Kanemoto, Norito,Kinda, Tomohiro,Yamamoto, Hiroki
, p. 1081 - 1085 (2007/10/03)
In order to synthesize four stereoisomers of cystathionine (CYT), D- and L-homocysteines (D- and L-Hcy) were synthesized from methionine (Met) by a facile procedure. L-Met was reacted with dichloroacetic acid in concentrated hydrochloric acid under reflux to give (4S)-1,3-thiazane-2,4-dicarboxylic acid hydrochloride [(4S)-TDC? HCl]. L-Hcy was obtained by treatment of (4S)-TDC? HCl with hydroxylamine. D-Hcy was also synthesized from D-Met via (4R)-TDC? HCl intermediate. The obtained D- and L-Hcy were condensed with (R)- and (S)-2-amino-3-chloropropanoic acid hydrochlorides under alkaline conditions to give four stereoisomers of CYT.
Synthesis of highly enantio-enriched α-amino acids by carboxylation of N-(α-lithioalkyl)oxazolidinones
Jeanjean, Fabien,Fournet, Guy,Bars, Didier Le,Gore, Jacques
, p. 1297 - 1305 (2007/10/03)
N-(α-Stannylalkyl)oxazolidinones can be obtained as a mixture of diastereomers in three steps from aldehydes with yields dependent on the R group of R-CHO. They can be transformed by a tin-lithium exchange to N-(α- lithioalkyl)oxazolidinones which equilibrate rapidly to one diastereomer. These compounds give rise, after carboxylation, to the diastereopure N-(α- carboxyalkyl)oxazolidinones. Transformation of the oxazolidinone moiety to a free amino group is accomplished by a Birch-type reduction. Using this method, L-methionine, L-alanine, L-leucine and L-homocysteine were obtained in good yields and ee = 92% to 95%. The short time required for the whole sequence makes this method ideal for synthesising 1-[11C]amino acids.
Preparations of Optically Active Homocysteine and Homocystine by Asymmetric Transformation of (RS)-1,3-Thiazane-4-carboxylic Acid
Miyazaki, Hideya,Ohta, Atsushi,Kawakatsu, Nobuyuki,Waki, Yukitaka,Gogun, Yasuhiro,et al.
, p. 536 - 540 (2007/10/02)
DL-Homocysteine from (RS)-homocysteine thiolactone hydrochloride was subjected to reaction with formaldehyde in acetic acid to give (RS)-1,3-thiazane-4-carboxylic acid monohydrate .An asymmetric transformation of (RS)-THA*H2O was achieved via salt formation with optically active tartaric acid in the presence of salicylaldehyde in acetic acid.The (R)- and (S)-THA obtained, respectively, from the salt of (R)-THA with (2R,3R)-tartaric acid and its enantiomeric salt were treated with hydroxylamine hydrochloride to give D- and L-Hcy of 100percent optical purity, respectively, in 50percent yield from (RS)-HTL*HCl.Oxidation of D- and L-Hcy with hydrogen peroxide gave D- and L-homocystine, respectively, in 47percent yield.
Syntheses of S-Substituted L-Homocysteine Derivatives by Cystathionine γ-Lyase of Streptomyces phaeochromogenes
Kanzaki, Hiroshi,Kobayashi, Michihiko,Nagasawa, Toru,Yamada, Hideaki
, p. 391 - 398 (2007/10/02)
Cystationine γ-lyase from Streptomyces phaeochromogenes catalyzes not only the α,γ-elimination rection of L-cystathionine, but also the γ-replacement reaction of L-homoserine in the presence of thiol compounds.Substrates for the enzyme in the γ-replacement reaction were examined.It was found that D-cysteine, L- and D-homocysteine, and 3- and 2-mercaptopropionate served as preferable substrates in the γ-replacement reaction.D-Allocystathionine, L- and mesohomolanthionine, S-carboxyethyl-L-homocysteine and S-methylcarboxymethyl-L-homocysteine were enzymatically synthesized from L-homoserine and the corresponding thiol compounds.The thus synthesized S-substituted L-homocysteine derivatives were isolated from large scale reaction mixtures and identified physicochemically.
Diastereospecific, Enzymically Catalysed Transmethylation from S-Methyl-L-methionine to L-Homocysteine, a Naturally Occuring Process
Grue-Soerensen, Gunnar,Kelstrup, Ebbe,Kjaer, Anders,Madsen, Joergen Oegaard
, p. 1091 - 1097 (2007/10/02)
A known catabolic pathway of S-methyl-L-methionine in higher plants: donation of a methyl group to L-homocysteine resulting in the production of two molecules of L-methionine, is subjected to stereochemical studies.The two, diastereoisomeric (2-2H, methyl-13C)-S-methyl-L-methionines are synthesized and utilised in transmethylation reactions with L-homocysteine as the acceptor and an enzyme preparation from jack beans as a catalyst.The resulting, variously labelled methionine species are converted into butyl esters of the N-trifluoroacetylated derivatives and, as such, subjected to g.l.c. combined with mass spectrometry in two ionisation modes.Experimentally determined parameters such as mass peack intensities, isotopic enrichment factors, diastereoisomeric purities, and protein-derived methionine, are utilised for calculating the stereoselectivity in the enzyme transfer of the diastereoisotopic methyl groups from S-methyl-L-methionine to L-homocysteine.Together, the independent results from the two series of diastereoisomers reveal an enzymatic preference of the pro-(R)-methyl group to the extent of 94percent or more.
