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Discadenin‐Derivate ohne cytokininaktiven Δ 2 ‐Isopentenylrest
Author(s) -
Seela Frank,
Hasselmann Doris
Publication year - 1980
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19801130542
Subject(s) - chemistry , alkylation , residue (chemistry) , protonation , derivative (finance) , stereochemistry , medicinal chemistry , organic chemistry , catalysis , ion , financial economics , economics
Discadenine Derivatives without Cytokinine Active Δ 2 ‐Isopentenyl Residue Alkylation of adenine with ethyl 4‐bromo‐2‐ L ‐phthalimidobutyrate yields the N ‐3‐alkylated derivative 4a . After removal of the protecting groups in 4a L ‐(+)‐discadenine without cytokinine active N 6 −Δ 2 ‐isopentenyl residue ( 3a ) is obtained. It shows similar inhibition of the spore germination as L ‐(+)‐discadenine ( 1 ). The derivatives 3b and c with modifications in the N ‐3 side chain are prepared analogously. The p K a value of 5.67 implies that protonation around the physiological pH value plays a key role in the biosynthesis and the regulatory function of discadenine.