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Über die Wirkung von symmetrischen 1,2‐Dialkylhydrazinen auf Carbonylverbindungen und Amin‐oxydasen. 16. Mitteilung über Amin‐oxydasen
Author(s) -
Carbon John A.,
Burkard Willy P.,
Zeller E. Albert
Publication year - 1958
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19580410642
Subject(s) - chemistry , benzaldehyde , aldehyde , acetaldehyde , ketone , nucleophile , electrophile , medicinal chemistry , monoamine oxidase , stereochemistry , enzyme , organic chemistry , catalysis , ethanol
1 The pI 50 ‐values of 1,2‐dimethyl‐, 1,2‐diethyl‐ and 1,2‐dipropyl‐hydrazine are of the order 4,7 for monoamine oxidase (MO) and about 5,8 for diamine oxidase (DO). For both enzymes the pI 50 ‐values of 1,2‐diisopropylhydrazine are much smaller 30 ). 2 Under conditions similar to those of the enzyme determinations, acetaldehyde reacts non‐enzymically with the first three 1,2‐dialkyl derivatives mentioned above, whilst 1,2‐diisopropylhydrazine remains inert during the spectrophotometric analysis. 3 In similar systems, 1,2‐dimethylhydrazine reacts slowly with benzaldehyde. 4 From these observations, and from data obtained in the literature concerning transannular bond formation, it is concluded that 1,2‐dialkylhydrazines react on MO and DO by virtue of their nucleophilic nature. The electrophilic counterpart of the active surface of the enzyme seems to be an aldehyde group in DO and a non‐aldehyde and non‐ketone carbonyl residue in MO and DO.