Biosynthetic potential of sesquiterpene synthases:: Alternative products of tobacco 5-epi-aristolochene synthase

被引：35

作者：

O'Maille, Paul E.

Chappell, Joe

Noel, Joseph P.

机构：

[1] Salk Inst Biol Studies, Howard Hughes Med Inst, Jack H Skirball Ctr Chem Biol & Proteom, La Jolla, CA 92037 USA

[2] Univ Kentucky, Dept Plant & Soil Sci, Lexington, KY 40546 USA

来源：

ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS | 2006年 / 448卷 / 1-2期

关键词：

sesquiterpene; terpene synthase; terpene cyclase; GC-MS; gas chromatography; biosynthesis; product identification; isomerization; enzyme mechanism; electrophilic cyclization;

D O I：

10.1016/j.abb.2005.10.028

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Nicotiana tabacum (tobacco) 5-epi-aristolochene synthase (TEAS) serves as all useful model for understanding the enzyme mechanisms of sesquiterpene biosynthesis. Despite extensive bio-chemical and structural characterization of TEAS, a more detailed analysis of the reaction product spectrum is lacking. This Study reports the discovery and quantification of several alternative sesquiterpene products generated by recombinant TEAS ill the single-vial GC-MS assay. The combined use of chiral and non-polar stationary phases for gas chromatography separations proved critical for resolving the numerous sesquiterpene products of TEAS for mass spectral analysis and identification. Co-injection Studies with available authentic standards from both synthetic and natural Sources further corroborated the assignment of several compounds., resulting ill an annotated reaction mechanism accounting for their biosynthesis. Moreover, a previously undocumented farnesyl trans-cis isomerization pathway was observed. (c) 2005 Elsevier Inc. All rights reserved.

引用

页码：73 / 82

页数：10

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