The stereospecificity of α-chymotrypsin-catalysed hydrolysis and alcoholysis of specific ester substrates

Halpern, B.; Ricks, Jeffrey; Westley, JW

doi:10.1071/ch9670389

Cited by 4 publications

(2 citation statements)

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“…All compounds were prepared by procedures previously described, and the configurational assignment under each chromatographic peak was made by synthesis of the optically pure diastereoisomers (7,8). All derivatives were characterized by mass spectrometry using a Beckman Time of Flight mass spectrometer and a Varían Aerograph 600D gas chromatograph coupled to a Finnigan 1015 Quadropole mass spectrometer.…”

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confidence: 99%

Effect of solute structure on separation of diastereoisomeric esters and amides by gas-liquid chromatography

Westley¹,

Halpern²,

Karger³

1968

Anal. Chem.

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The separation of diastereoisomers by gas-liquid chromatography (GLC) is an area currently being actively investigated {1-4), since the method can be successfully used for the determination of steric purity of asymmetric compounds (5). We have been concerned with the underlying solute structural features necessary for separation to occur {6, 7), in order to provide guidelines for the selection of suitable resolving agents and chromatographic conditions. In this paper we wish to report results on the separation of a series of systematically structurally related A-trifluoroacetyl-X-phenylalanine ± alkyl esters and a series of A-trifluoroacetyl-S-prolylamides derived from asymmetric amines and amino acid esters. EXPERIMENTAL Diastereoisomeric esters were separated on a Varían Autoprep gas chromatograph using a 15-foot X V-i-inch column packed with 0.75/0.25 W/W% (DEGS)/(EGSS-X) on Chromosorb W, with a nitrogen flow of 65 ml/min (Table I). The amide and peptide derivatives were chromatographed on a Varían Aerograph 1200 chromatograph using 5-foot X Vs-inch stainless steel columns packed with 5% (QF-1) on Aeropack 30 and 0.5% ethylene glycol adipate (EGA) on Aeropack 30, with a nitrogen flow of 30 ml/min (Table II).

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confidence: 99%

Effect of solute structure on separation of diastereoisomeric esters and amides by gas-liquid chromatography

Westley¹,

Halpern²,

Karger³

1968

Anal. Chem.

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“…Menthol had been used previously for the crystallization, separation, , and determination of enantiopurity of subsequent esters. In this study, we were pleased to observe (Scheme ) that the 1:1 mixture of diastereomers of the α-aminated menthyl esters were readily separable by preparatory column chromatography.…”

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confidence: 99%