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Synthesis of gibberellin A 29 β‐ D ‐glucosides and β‐ D ‐glucosyl derivatives of [17‐ 13 C,T 2 ]gibberellin A 5 , A 20 , and A 29
Author(s) -
Schneider Gernot,
Schreiber Klaus,
Jensen Einar,
Phinney Bernard O.
Publication year - 1990
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199019900192
Subject(s) - chemistry , gibberellin , stereochemistry , botany , biology
Abstract 2‐ O ‐GA 29 β‐ D ‐glucopyranoside ( 1e ) and 13‐ O ‐GA 29 , β‐ D ‐glucopyr‐anoside ( 1h ) were synthesized from GA 29 methyl ester ( 1b ). Their structures were confirmed by 1 H NMR and GC‐MS. Likewise, [17‐ 13 C,T 2 ]‐labelled 1e and 1h could be obtained. From [17‐ 13 C,T 2 ]GA 20 ( 2a ) and [17‐ 13 C,T 2 ]GA 5 ( 3a ) the 13‐ O ‐GA β‐ D ‐[6‐D 2 ]glucopyranosides [17‐ 13 C,T 2 ;6′‐D 2 ]‐ 2d and [17‐ 13 C,T 2 ;6′‐D 2 ]‐ 3d , and the β‐ D ‐glucopyranosyl esters [17‐ 13 C,T 2 ;6′‐D 2 ]‐ 2f and [17‐ 13 C,T 2 ;6′‐D 2 ]‐ 3f were synthesized. The labelled compounds were characterized by HPLC and GC‐MS.