13850-19-6

Upstream product

• 150-97-0 D,L-mevalonic acid 
• 6090-70-6 sodium mevalonate 
• 21561-90-0 C₂₀H₃₆O₇P₂ 
• 28235-66-7 ent-15-Kauren-6α,20-diol 
• 90457-97-9 ent-kauran-17-ol 
• 36146-33-5 ent-15-Kauren-6-on-20-al 
• 112609-07-1 ent-17-iodokaurane 

Downstream Products

• 10179-10-9 ent-15α-hydroxykaurene 
• 4608-45-1 C₂₀H₃₁Br 
• 40140-48-5 C₂₆H₃₈N₂O₂S 
• 16836-31-0 16α,17-ent-kauranediol 
• 14696-33-4 ent-kaur-15-en-17-ol 
• 2359-73-1 (+)-hibaene 
• 16836-31-0 Kauran-16,17-diol 
• 5354-44-9 kauranol 
• 42753-28-6 ent-kauran-16β,17-epoxide 
• 10438-44-5 (-)-kaur-16-en-19-ol 
• 5282-24-6 ent-kaur-16-en-19-al 
• 5095-09-0 kaurenoic acid 
• 10179-10-9 (-)-Kauren-(16)-ol-(15α) 
• 4627-79-6 C₂₀H₃₂O 

Relevant academic research and scientific papers

Functional characterization of wheat ent-kaurene(-like) synthases indicates continuing evolution of labdane-related diterpenoid metabolism in the cereals

Wheat (Triticum aestivum) and rice (Oryza sativa) are two of the most agriculturally important cereal crop plants. Rice is known to produce numerous diterpenoid natural products that serve as phytoalexins and/or allelochemicals. Specifically, these are labdane-related diterpenoids, derived from a characteristic labdadienyl/copalyl diphosphate (CPP), whose biosynthetic relationship to gibberellin biosynthesis is evident from the relevant expanded and functionally diverse family of ent-kaurene synthase-like (KSL) genes found in rice the (OsKSLs). Herein reported is the biochemical characterization of a similarly expansive family of KSL from wheat (the TaKSLs). In particular, beyond ent-kaurene synthases (KS), wheat also contains several biochemically diversified KSLs. These react either with the ent-CPP intermediate common to gibberellin biosynthesis or with the normal stereoisomer of CPP that also is found in wheat (as demonstrated by the accompanying paper describing the wheat CPP synthases). Comparison with a barley (Hordeum vulgare) KS indicates conservation of monocot KS, with early and continued expansion and functional diversification of KSLs in at least the small grain cereals. In addition, some of the TaKSLs that utilize normal CPP also will react with syn-CPP, echoing previous findings with the OsKSL family, with such enzymatic promiscuity/elasticity providing insight into the continuing evolution of diterpenoid metabolism in the cereal crop plant family, as well as more generally, which is discussed here.

Functional characterization of wheat ent-kaurene(-like) synthases indicates continuing evolution of labdane-related diterpenoid metabolism in the cereals

Wheat (Triticum aestivum) and rice (Oryza sativa) are two of the most agriculturally important cereal crop plants. Rice is known to produce numerous diterpenoid natural products that serve as phytoalexins and/or allelochemicals. Specifically, these are labdane-related diterpenoids, derived from a characteristic labdadienyl/copalyl diphosphate (CPP), whose biosynthetic relationship to gibberellin biosynthesis is evident from the relevant expanded and functionally diverse family of ent-kaurene synthase-like (KSL) genes found in rice the (OsKSLs). Herein reported is the biochemical characterization of a similarly expansive family of KSL from wheat (the TaKSLs). In particular, beyond ent-kaurene synthases (KS), wheat also contains several biochemically diversified KSLs. These react either with the ent-CPP intermediate common to gibberellin biosynthesis or with the normal stereoisomer of CPP that also is found in wheat (as demonstrated by the accompanying paper describing the wheat CPP synthases). Comparison with a barley (Hordeum vulgare) KS indicates conservation of monocot KS, with early and continued expansion and functional diversification of KSLs in at least the small grain cereals. In addition, some of the TaKSLs that utilize normal CPP also will react with syn-CPP, echoing previous findings with the OsKSL family, with such enzymatic promiscuity/elasticity providing insight into the continuing evolution of diterpenoid metabolism in the cereal crop plant family, as well as more generally, which is discussed here.

ent-Kaurene and squalene synthesis in Fusarium fujikuroi cell-free extracts

Sterols and gibberellins are the main terpenoids in the Ascomycete Fusarium fujikuroi. Their respective precursors squalene and ent-kaur-16-ene (henceforth called kaurene) were the main terpenoids synthesised from radioactive mevalonate by extracts of F. fujikuroi in vitro. Kaurene predominated when the extracts were obtained from mycelia engaged in gibberellin production. Squalene predominated in all other cases, and particularly when the extracts were obtained from mutants with various defects in gibberellin synthesis or nitrogen-fed wild-type cultures. New protein synthesis was required to maintain the production of gibberellins in vivo and of kaurene in vitro, but not to maintain the capacity to produce squalene in vitro. Addition of a nitrogen source to cultures engaged in gibberellin production caused a large, transient increase in the mycelial concentration of L-glutamine and abolished the accumulation of gibberellins immediately and the capacity to produce kaurene later. (C) 2000 Elsevier Science Ltd.

Synthesis of ent-Kaurene from a Naturally Occurring Precursor

ent-Kaurene (1) has been synthesized from a naturally occurring precursor, ent-kaurane-17,19-diol (3a).Selective deoxygenation at C19 of the diol was achieved after the C17 hydroxyl was protected as the triphenylmethyl ether. ent-Kaurene was then prepared by way of an elimination sequence at C17.

BIOSYNTHESIS OF GIBBERELLIN A12-ALDEHYDE, GIBBERELLIN A12 AND THEIR KAURENOID PRECURSORS FROM MEVALONIC ACID IN A CELL-FREE SYSTEM FROM IMMATURE SEED OF PHASEOLUS COCCINEUS

A cell-free system capable of gibberellin (GA) biosynthesis has been prepared from immature seed of Phaseolus coccineus.This system converted mevalonic acid (MVA) to ent-kaurene, ent-kaurenoic acid, ent-kauradienoic acid, ent-7α-hydroxykaurenoic acid, ent-6α,7α-dihydroxykaurenoic acid, GA12-aldehyde and GA12. ent-Kaurene was converted to ent-kaurenol, ent-kaurenal, ent-kaurenoic acid and ent-7α-hydroxykaurenoic acid.All identifications were by GC/MC.The pathway from MVA to GA12-aldehyde in this species thus appears to be the same as that found in cell-free preparations derived from immature seed of other species.Key Word Index-Phaseolus coccineus; Leguminosae; runner bean; seed development; biosynthesis; cell-free system; HPLC; GC/MC; gibberellin.