Biosynthesis of monoterpenes: Stereochemical implications of acyclic and monocyclic olefin formation by (+)- and (−)-pinene cyclases from sage *
Rodney Croteau,D M Satterwhite +1 more
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TLDR
Results indicate that the alternate substrates are ionized by the cyclases prior to their achieving the optimum orientation for bicyclization.About:
This article is published in Journal of Biological Chemistry.The article was published on 1989-09-15 and is currently open access. It has received 31 citations till now. The article focuses on the topics: Geranyl pyrophosphate & Pyrophosphate.read more
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Journal ArticleDOI
4S-limonene synthase from the oil glands of spearmint (Mentha spicata). cDNA isolation, characterization, and bacterial expression of the catalytically active monoterpene cyclase.
TL;DR: Sequence comparisons with a sesquiterpene cyclase, epi-aristolochene synthase from tobacco, and a diterPene cyclases demonstrated a significant degree of similarity between these three terpenoid cyclase types, the first three examples of this large family of catalysts to be described from higher plants.
Journal ArticleDOI
Truncation of limonene synthase preprotein provides a fully active 'pseudomature' form of this monoterpene cyclase and reveals the function of the amino-terminal arginine pair.
TL;DR: A role for the tandem arginines in the unique diphosphate migration step accompanying formation of the intermediate 3S-linalyl diph phosphate and preceding the final cyclization reaction catalyzed by the monoterpene synthases is indicated.
PatentDOI
Monoterpene synthases from grand fir (abies grandis)
TL;DR: In this paper, a system and methods for the recombinant expression of recombinant monoterpene synthases that may be used to facilitate their production, isolation and purification in significant amounts are provided.
Journal ArticleDOI
Enantiomeric natural products: occurrence and biogenesis.
Jennifer M. Finefield,David H. Sherman,Martin Kreitman,Robert M. Williams,Robert M. Williams +4 more
TL;DR: In nature, chiral natural products are usually produced in optically pure form-however, occasionally both enantiomers are formed; these enantiomeric natural products can arise from a single species or from different genera and/or species.
PatentDOI
Monoterpene synthases from common sage (Salvia officinalis)
TL;DR: In this paper, a cDNAs encoding (+)-bornyl diphosphate synthase, 1-8cineole synthase and (+)-sabinene synthase from common sage (Salvia officinalis) have been isolated and sequenced, and corresponding amino acid sequences have been determined.
References
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Journal ArticleDOI
When is an intermediate not an intermediate? Enforced mechanisms of general acid-base, catalyzed, carbocation, carbanion, and ligand exchange reaction
Journal ArticleDOI
Isoprenoid biosynthesis. Stereochemistry of the cyclization of allylic pyrophosphates
Journal ArticleDOI
Pinene cyclases I and II. Two enzymes from sage (Salvia officinalis) which catalyze stereospecific cyclizations of geranyl pyrophosphate to monoterpene olefins of opposite configuration.
H Gambliel,R Croteau +1 more
TL;DR: A soluble enzyme preparation from immature sage leaves has been shown to catalyze the cation-dependent cyclization of geranyl pyrophosphate to the isomeric monoterpene olefins (+/-)-alpha-pinene and (-)-beta- pinene and to lesser amounts of camphene and limonene.
Journal ArticleDOI
Biosynthesis of monoterpenes: Preliminary characterization of bornyl pyrophosphate synthetase from sage (Salvia officinalis) and demonstration that geranyl pyrophosphate is the preferred substrate for cyclization
Rodney Croteau,Frank Karp +1 more
TL;DR: Bornyl pyrophosphate synthetase is the first monoterpene synthet enzyme to be isolated free from competing phosphatases, and the first to show a strong preference for geranyl pyroph phosphate as substrate.
Related Papers (5)
Pinene cyclases I and II. Two enzymes from sage (Salvia officinalis) which catalyze stereospecific cyclizations of geranyl pyrophosphate to monoterpene olefins of opposite configuration.
H Gambliel,R Croteau +1 more