Über die Reaktion des Ninhydrins und Isatins mit Prolin und Oxyprolin

Gräßmann, W.; Arnim, K.

doi:10.1002/jlac.19345090121

Cited by 41 publications

(12 citation statements)

References 9 publications

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“…Per tube: L-glutamic acid, 65 ,umoles; pyridoxal phosphate, 10-5 M; MgCl2, 50 ,moles; KH2PO4, 50 ,moles; ATP, sodium salt, 15 umoles; ADP, sodium salt, 15 ,umoles; M/15 pH 7.5 tris buffer; dialyzed sonic extract equivalent to 1.0 mg whole cell N. Reaction time, 120 min. Arnim, 1934). As a result of these findings the unknown reaction product of glutamic acid was identified as z\l-pyrroline-5-carboxylic acid.…”

Section: 3mentioning

confidence: 91%

Amino Acid Metabolism by Pleuropneumonialike Organisms Iii

Smith

1957

J Bacteriol

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The activity of resting cell suspensions of pleuropneumonialike organisms of human origin towards glutamic acid has been reported to be relatively poor when compared with the activity towards glutamine (Smith, 1955a). Although glutamine is rapidly deamidated to yield glutamic acid as one of the end products, the glutamic acid disappears very slowly. No a-ketoglutaric acid was detectable following the utilization of glutamic acid. However, a compound was formed in increasing amounts which gave a positive reaction with isatin. Either glutamine or glutamic acid were growth requirements in synthetic media (Smith, 1955b). No transaminase activity was demonstrable by these organisms when a-ketoglutaric acid was employed as the amino acceptor or glutamic acid as the amino donor. (Smith, 1955a). The following report presents an extended study on the fate of glutamic acid in these organisms. It was shown that glutamic acid is utilized primarily in anabolic rather than catabolic processes. MATERIAL AND METHODS Strain 39 was used exclusively in this study because of its ease of growth in large quantity and because of its ability to multiply in synthetic media (Smith, 1955b). Cells were grown and harvested as previously described (Smith, 1955a). Cell free extracts were prepared by subjecting suspensions of washed whole cells containing 1 or 2 mg cellular nitrogen per ml in M/15 phosphate or tris (hydroxymethylaminomethane) buffers to sonic vibrations in a 9-Kc Raytheon magnetoconstriction oscillator for a period of 20 min. Cellular debris was removed by centrifugation at 13,000 rpm for 5 min in a Servall angle centrifuge. Cell extracts were dialyzed against pH 7.5 tris buffer at 4 C. ' This work was supported in part by a contract [Nonr 551(04)] between the Office of Naval Research and the University of Pennsylvania.

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Section: 3mentioning

confidence: 91%

Amino Acid Metabolism by Pleuropneumonialike Organisms Iii

Smith

1957

J Bacteriol

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“…Parent cyclopropene ( 3a ) was obtained according to a literature procedure with slight modifications . 2-(3,4-Dihydro-2 H -pyrrol-1-ium-1-yl)-1-oxo-1 H -inden-3-olate (DHPO, 6 ) was synthesized by the method of Grassmann and Arnim …”

Section: Methodsmentioning

confidence: 99%

Stereo- and Regioselective 1,3-Dipolar Cycloaddition of the Stable Ninhydrin-Derived Azomethine Ylide to Cyclopropenes: Trapping of Unstable Cyclopropene Dipolarophiles

et al. 2019

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A stereo- and regioselective 1,3-dipolar cycloaddition of the stable ninhydrin-derived azomethine ylide [2-(3,4-dihydro-2H-pyrrolium-1-yl)-1-oxo-1H-inden-3-olate, DHPO] to differently substituted cyclopropenes has been established. As a result, an efficient synthetic protocol was developed for the preparation of biologically relevant spiro[cyclopropa[a]pyrrolizine-2,2′-indene] derivatives. DHPO has proved to be an effective trap for such highly reactive and unstable substrates as parent cyclopropene, 1-methylcyclopropene, 1-phenylcyclopropene, and 1-halo-2-phenylcyclopropenes. It has also been found that 3-nitro-1,2-diphenylcyclopropene undergoes a nucleophilic substitution reaction in alcohols and thiols to afford 3-alkoxy- and 3-arylthio-substituted 1,2-diphenylcyclopropenes, which can be captured as corresponding 1,3-dipolar cycloadducts in the presence of DHPO. These new approaches provide a straightforward strategy for the synthesis of functionally substituted cyclopropa[a]pyrrolizine derivatives. The factors governing regio- and stereoselectivity have been revealed by means of quantum mechanical calculations (M11 density functional theory), including previously unreported N ylide–H cyclopropene second-orbital interactions. The outcome of this work contributes to the study of 1,3-dipolar cycloaddition, as well as enriches chemistry of cyclopropenes and methods for the construction of polycyclic compounds with cyclopropane fragments.

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“…Rmines are added in position 4 (25,26), in the case of the 4-sulfonate with the simultaneous liberation of bisulfite (27). It is, however, not quite clear whether the mechanism of the reaction with amino acids and, in particular, of the concomitant liberation of COZ is similar to that formulated for ninhydrin (20,21). Compare also the observations on the reaction between proteins and ninhydrin (28) and 1,2-naphthoquinone-4-sulfonic acid (29).…”

mentioning

confidence: 97%

“…This effect has been shown for chloramine-T (18), 1,2-naphthoquinone-4-sulfonic acid ( 19)) ninhydrin (20,21), and alloxan (22). For purposes of comparison the action on alanine of some of the clotting agents and also of several carbonyl compounds devoid of coagulant activity was studied.…”

mentioning

confidence: 97%