468-44-0Relevant articles and documents
Probing the mechanism of loss of carbon-20 in gibberellin biosynthesis. Synthesis of gibberellin 3α,20-hemiacetal and 19,20-lactol analogues and their metabolism by a recombinant GA 20-oxidase
Ward, Jane L.,Gaskin, Paul,Brown, Robert G. S.,Jackson, Graham S.,Hedden, Peter,Phillips, Andy L.,Willis, Christine L.,Beale, Michael H.
, p. 232 - 241 (2007/10/03)
A gibberellin 3α,20-hemiacetal,1 (equivalent to 3-epi-gibberellin A36), has been synthesised from gibberellin A13. Turnover of this hemiacetal by recombinant gibberellin 20-oxidase occurred with loss of the 20-carbon atom to give the 20-nor-19,10-lactone (3-epi-gibberellin A4). In addition, two other enzyme products were detected and identified by synthesis as 3-epi-20-norgibberellin A13 and 3-epi-1,10-didehydro-20-norgibberellin A13. These by-products indicate that the enzymatic reaction proceeds via a C-10 radical intermediate. Carbon radicals at C-10 and acyl radicals at C-20 were generated chemically and their decomposition products were studied with reference to the biological mechanism. The corresponding 19-nor-3α,20-hemiacetal 3 and 19-methylene analogue 4 were synthesised but were not oxidised at C-20 by the enzyme. These results indicate that the 19-carboxylic acid is an essential component of the enzyme reaction.
METHYLENATION OF CARBONYL COMPOUNDS WITH Zn-CH2Br2-TiCl4.APPLICATIONS TO GIBBERELLINS
Lombardo, Luciano
, p. 4293 - 4296 (2007/10/02)
A highly active species prepared from Zn-CH2Br2-TiCl4 reacted instantaneously with aldehydes and ketones to give methylenated products with exceptional selectivity.
STEREOSELECTIVE REDUCTION OF 3-KETO GIBBERELLIN ACIDS TO 3β-OLS USING K-SELECTRIDE WITH KH2PO4 BUFFER
Bell, Russell A.,Turner, John V.
, p. 4871 - 4872 (2007/10/02)
KH2PO4 buffered K-Selectride gives with 3-keto gibberellin acids, borates which are reduced stereoselectively to 3β-ols.