Resolution of Glutamic Acid with 1-Hydroxy-2-aminobutane^1,2

Abstract

Unsubstituted DL-glutamic acid has been resolved by use of an optical isomer of the readily available l-hydroxy-2-aminobutane. The amine used was obtained by resolution with either tartaric acid or glutamic acid. Attempts to extend this method to aspartic acid resulted in partial resolution only. Formyl-DL-phenylalanine, however, was resolved to give the pure isomers readily. Mutual solubilizing effects are described for diastereomers of the hydroxybutaneammonium hydrogen glutamate.

Separation of racemic mixtures: optical resolution of DL-2-amino-1-butanol

“…Ternary Equilibrium Data for l( + )-2-Amino-l-butanol-L( + )-hemitartarate (I)- "mf = mass fraction (-)-2-amino-l-butanol-L(+)-hemitartarate (II). This observation is in agreement with the trend previously reported by Radke et al (1954) and by many patentees.…”

“…The solvents employed are water and different alkanols. The information available on the process is, however, very limited (Radke et al, 1954;Pitre and Grabitz, 1969) and is found mostly in the patent literature (Zoja, 1971;Seres and Daroczi, 1970;Ichikawa et al, 1975).…”

Enzyme inhibitors. 25. Equation to calculate the unknown Ki from two known values of Ki in an R,S, and RS series. Stereoselectivity of inhibition of adenosine deaminase by (R)-, (S)-, and (RS)-9-(1-hydroxy-2-alkyl and -aralkyl)adenines

“…(DL) = (D) + 0) Adl Ad Kl Solving eq 7 for ADL gives eq 8 which describes the relationship of the dissociation constant of the racemic compound to its enantiomers for competitive enzyme inhibitors. § ^DL "" 2 KDKL KO+KL (8) The dissociation constants for the racemic compounds were calculated from eq 8 using the experimental data presented in Table I. In all cases, the caled A,'s for the racemic compound agree well with the found values (see Table I).…”

Neue Antipodenpaare zur optischen Spaltung recemischer Basen

“…(R)-( -)-2-Anziizobutanol-(l) wird analog aus dem Salz des (I? )-( -)-2-Aniino-t)utanols-(l) mit l a erhalten: [a],:: = -10,lO" ( d = 0,940); Litcratunvert[6]:[cr],;: = -9,92" (d = 0,939). Ofitische Spaltiwzg voiz (R) ( S ) -( / -l~h e n~~l -d t h y I ) -a r n i n init I b und I n .…”

“…Das einfache und effektive chromatographische Verfahren hat sich bei der Synirhese von [S a-14C]-Biopterin bewahrt [5]. Es erlaubte erstmals die Reindarstellung und damit die Charakterisierung des Neopterins und seiner drei optischen Isomeren [6] und spater auch der drei optischen Isomeren des Biopterins [7]. Es wurde auch bei der Darstellung von Aminobiopterin und Aminoneopterin erfolgreich angewandt [8].…”