1069-31-4Relevant articles and documents
Highly enantioselective synthesis of non-natural aliphatic α-amino acids via asymmetric hydrogenation
Ji, Jianjian,Chen, Caiyou,Cai, Jiayu,Wang, Xinrui,Zhang, Kai,Shi, Liyang,Lv, Hui,Zhang, Xumu
supporting information, p. 7624 - 7627 (2015/07/15)
By employing a rhodium-Duanphos complex as the catalyst, β-alkyl (Z)-N-acetyldehydroamino esters were smoothly hydrogenated in a highly efficient and enantioselective way. Excellent enantioselectivities together with excellent yields were achieved for a series of substrates. An efficient approach for the synthesis of the intermediate of the orally administered anti-diabetic drugs Alogliptin and Linagliptin in the DPP-4 inhibitor class was also developed.
Biosynthesis of blasticidin S from L-α-arginine. Stereochemistry in the arginine-2,3-aminomutase reaction
Prabhakaran,Woo,Yorgey,Gould
, p. 5785 - 5791 (2007/10/02)
A series of labeled α-arginines have been fed to fermentations of Streptomyces griseochromogenes in order to examine the mechanism of L-β-arginine formation in the biosynthesis of the antibiotic blasticidin S. [3-13C,2-15N]Arginine was synthesized and fed; analysis of the derived antibiotic by 13C NMR spectroscopy revealed the retention of the original α-nitrogen and its intramolecular migration to the β-position, revealing the presence of an arginine-2,3-aminomutase. Feedings of [2,3,3-2H3]-, [3,3-2H2]-, and [2-2H]arginines revealed the complete retention of the original β-hydrogens with migration of one to the α-position, as well as partial loss of the original α-hydrogen presumably due to arginine racemase activity. (3R)-[3-2H]- and (3S)-[3-2H]arginines were synthesized unambiguously and used to determine that the pro-3R hydrogen of α-arginine migrates to the α-position (C-2). δ-N-[13CH3]Methylarginine was synthesized, mixed with [guanidino-14C]arginine, and fed to S. griseochromogenes. A 42% incorporation of radioactivity from arginine was obtained, but no 13C enrichment was observed in the blasticidin S sample, indicating that arginine, itself, is the aminomutase substrate.
Aminosaeuren, I. Darstellung von Aminosaeuren aus Halogencarbonsaeure-alkylestern mit Alkalimetallcyanaten
Effenberger, Franz,Drauz, Karlheinz,Foerster, Siegfried,Mueller, Wolfgang
, p. 173 - 189 (2007/10/02)
α- and ω-halo- as well as α,ω-dihalocarboxylic alkyl esters react with potassium cyanate in the presence of alcohol at 80 - 120 deg C in dipolar aprotic solvents to yield α- and ω-(alkoxycarbonylamino)- and α,ω-bis(alkoxycarbonylamino)carboxylic alkyl esters, respectively, in good yields.Hydrolytic cleavage of these mono- or diurethanes with an aqueous solution of hydrochloric acid/formic acid leads to the corresponding amino acid hydrochlorides in nearly quantitative yields.
