Biogenetic speculation and biosynthetic advances

Thomas, Robert

doi:10.1039/b311022m

Cited by 21 publications

(11 citation statements)

References 147 publications

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“…22 Speculation on the biosynthetic origin of alga-derived brominated terpenoids has recently been shown to be correct. 23 As can be seen, biogenetic hypotheses of the type in this paper has helped advance our understanding of biosynthetic processes in the past 24 and has assisted in the design of biomimetic syntheses. 25 …”

Section: Discussionmentioning

confidence: 85%

Spontaneity in the patellamide biosynthetic pathway

et al. 2006

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Post-translationally modified ribosomal peptides are unusual natural products and many have potent biological activity. The biosynthetic processes involved in their formation have been delineated for some, but the patellamides represent a unique group of these metabolites with a combination of a macrocycle, small heterocycles and D-stereocentres. The genes encoding for the patellamides show very low homology to known biosynthetic genes and there appear to be no explicit genes for the macrocyclisation and epimerisation steps. Using a combination of literature data and large-scale molecular dynamics calculations with explicit solvent, we propose that the macrocyclisation and epimerisation steps are spontaneous and interdependent and a feature of the structure of the linear peptide. Our study suggests the steps in the biosynthetic route are heterocyclisation, macrocyclisation, followed by epimerisation and finally dehydrogenation. This study is presented as testable hypothesis based on literature and theoretical data to be verified by future detailed experimental investigations.

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Section: Discussionmentioning

confidence: 85%

Spontaneity in the patellamide biosynthetic pathway

et al. 2006

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“…The latter postulated epoxyanthraquinone pathway uses two successive 1,2‐shifts and leads to phenanthraquinones; it is allied to the previously proposed epoxide‐driven rearrangement involved in the biosynthesis of the spiro mode‐S‐folded fused‐ring streptomycete PK fredericamycin A ( 40 ; Scheme ) . Based on [ 13 C 2 ]acetate feeding studies, 40 was initially thought to form from two PK chains .…”

Section: Candidate Exceptions To the Biosynthetic Classification Of Fmentioning

confidence: 95%

“…In addition to the putative biosynthesis of fused‐ring PKs by iterative type I PKSs of fungi (e.g., chrysophanol 4 ) and type II PKSs of bacteria (e.g., chrysophanol 5 ), the formation of fused‐ring dodecaketides by type III PKSs has also been described . Type III PKS are predominantly of plant origin and catalyse the formation a wide diversity of structures ranging from common chalcones and stilbenes to the less abundant curcuminoids and phenylphenalenones …”

Section: Candidate Exceptions To the Biosynthetic Classification Of Fmentioning

confidence: 99%

Examination of Potential Exceptions to the F and S Biosynthetic Classification of Fused‐Ring Aromatic Polyketides

Thomas¹

2016

ChemBioChem

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The reported acetate-derived labelling of the fungal naphthalene γ-pyrone fonsecin, two streptomycete dodecaketide αpyrones TW93f and TW93g, and the streptomycete phenanthraquinones piloquinone, murayaquinone and haloquinone appear to be exceptions to the generalisation that fungi and streptomycetes produce fused-ring aromatic polyketides by different modes of cyclisation. A review of their 1) originally assigned formulae, 2) [ C ]acetate-derived labelling patterns, and 3) modes of cyclisation leads to the recognition of feasible alternative chemical structures or biosynthetic pathways, which are in accord with the originally proposed classification system.

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“…1 (groups A and B). All steroids of group A have also been oxidized at C-19 and are distributed into two series: 3a-oxysteroids (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11), and 3b-oxysteroids (12)(13)(14), three of them bear a C-19-C-6 oxygen bridge (9)(10)(11). The remaining 15-18 compose group B.…”

Section: Introductionmentioning

confidence: 99%