87563-33-5

Upstream product

• 130395-25-4 Malonic acid (E)-3-methyl-5-((1S,2R,4aR)-1,2,4a,5-tetramethyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-yl)-pent-2-enyl ester (E)-3-methyl-5-((S)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-pent-2-enyl ester 
• 6699-20-3 (E,E,E)-geranylgeranyl diphosphate 

Relevant academic research and scientific papers

A single residue change leads to a hydroxylated product from the class II diterpene cyclization catalyzed by abietadiene synthase

Class II diterpene cyclases catalyze bicyclization of geranylgeranyl diphosphate. While this reaction typically is terminated via methyl deprotonation to yield copalyl diphosphate, in rare cases hydroxylated bicycles are produced instead. Abietadiene synthase is a bifunctional diterpene cyclase that usually produces a copalyl diphosphate intermediate. Here it is shown that substitution of aspartate for a conserved histidine in the class II active site of abietadiene synthase leads to selective production of 8α-hydroxy-CPP instead, demonstrating striking plasticity.

TERPENOID COMPOUNDS FROM PARENTUCELLIA LATIFOLIA

Together with phytol, sitosterol acetate, α-tocopherylquinone annd sitosterol, the neutral part of Parentucellia latifolia afforded seven esters of diterpene alcohols: 7,13E-labdadien-15-ol acetate; ent-3,13E-clerodadien-15-ol acetat; di-malonate; 7,13E-labdadien-15-yl and ent-3,13E-clerodadien-15-yl malonic acid diester; di- malonate; 7,13E-labdadien-15-yl-methyl malonic acid diester; ent-3-13E-clerodadien-15-yl-methyl malonic acid diester.Three nor diterpenes: 14,15-dinor-7-labden-13-one; 14,15-dinor-ent-3-cleroden-13-one; 14,15-dinor-ent-2,4(18)clerodadien-13-one; and seven diterpene alcohols, five of them isolated as acetyl derivatives: 7,13E-labdadien-15-ol; ent-3,13E-clerodadien-15-ol; diacetate of 8,(17),13E-labdadien-7α,15-diol; 15-acetoxy-13E-labden-8β-ol; 15-acetoxy-13E-labden-8-ol and 15-acetoxy-ent-3,13E-clerodadien-2-one.