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1.
J Nat Prod ; 78(4): 645-52, 2015 Apr 24.
Article in English | MEDLINE | ID: mdl-25785712

ABSTRACT

Orbitides are short (5-11 amino acid residue), ribosomally synthesized homodetic plant cyclic peptides characterized by N-to-C amide bonds rather than disulfide bonds. Orbitides can be discovered using mass spectrometry of plant extracts or by identifying DNA sequences coding for the precursor protein. The number of orbitides that have been characterized to date, by a number of different research groups, is modest. The nomenclatural system currently used for the Type VI cyclic peptides has been developed in an ad hoc fashion and is somewhat arbitrary. We propose a systematic naming system specifically for the Type VI cyclic peptides that reflects the taxonomic name of the species producing the orbitides and a numbering system that enables systematic representation of amino acid residues and modifications. The proposed naming system emulates the IUPAC Nomenclature for Natural Products and UniProt, both of which use abbreviations of taxonomic names for the compounds in question. Nomenclature for post-translational modifications also follows the IUPAC precedent, as well as the cyclic peptide literature. Furthermore, the proposed system aims to maintain agreement with the precedents set by the pre-existing literature. An example of the proposed nomenclature is provided using the methionine-containing homodetic peptides of Linum usitatissimum (flaxseed).


Subject(s)
Oligopeptides/classification , Peptides, Cyclic/classification , Amino Acid Sequence , Base Sequence , Flax/chemistry , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Oligopeptides/chemistry , Peptides, Cyclic/chemistry
2.
Nat Prod Rep ; 30(1): 108-60, 2013 Jan.
Article in English | MEDLINE | ID: mdl-23165928

ABSTRACT

This review presents recommended nomenclature for the biosynthesis of ribosomally synthesized and post-translationally modified peptides (RiPPs), a rapidly growing class of natural products. The current knowledge regarding the biosynthesis of the >20 distinct compound classes is also reviewed, and commonalities are discussed.


Subject(s)
Biological Products , Peptides , Ribosomes/metabolism , Amino Acid Sequence , Biological Products/chemical synthesis , Biological Products/chemistry , Biological Products/classification , Biological Products/pharmacology , Humans , Molecular Sequence Data , Molecular Structure , Peptides/chemical synthesis , Peptides/chemistry , Peptides/classification , Peptides/pharmacology , Protein Processing, Post-Translational , Ribosomes/genetics
3.
Plant J ; 67(4): 682-90, 2011 Aug.
Article in English | MEDLINE | ID: mdl-21554452

ABSTRACT

Cyclic peptides (CPs) are produced in a very wide range of taxa. Their biosynthesis generally involves either non-ribosomal peptide synthases or ribosome-dependent production of precursor peptides. Plants within the Caryophyllaceae and certain other families produce CPs which generally consist of 5-9 proteinogenic amino acids. The biological roles for these CPs in the plant are not very clear, but many of them have activity in mammalian systems. There is currently very little known about the biosynthesis of CPs in the Caryophyllaceae. A collection of expressed sequence tags from developing seeds of Saponaria vaccaria was investigated for information about CP biosynthesis. This revealed genes that appeared to encode CP precursors which are subsequently cyclized to mature CPs. This was tested and confirmed by the expression of a cDNA encoding a putative precursor of the CP segetalin A in transformed S. vaccaria roots. Similarly, extracts of developing S. vaccaria seeds were shown to catalyze the production of segetalin A from the same putative (synthetic) precursor. Moreover, the presence in S. vaccaria seeds of two segetalins, J [cyclo(FGTHGLPAP)] and K [cyclo(GRVKA)], which was predicted by sequence analysis, was confirmed by liquid chromatography/mass spectrometry. Sequence analysis also predicts the presence of similar CP precursor genes in Dianthus caryophyllus and Citrus spp. The data support the ribosome-dependent biosynthesis of Caryophyllaceae-like CPs in the Caryophyllaceae and Rutaceae.


Subject(s)
Citrus/metabolism , Dianthus/metabolism , Peptides, Cyclic/biosynthesis , Plant Extracts/chemistry , Protein Precursors/genetics , Saponaria/metabolism , Amino Acid Sequence , Citrus/chemistry , Citrus/genetics , Consensus Sequence , DNA, Complementary/genetics , Dianthus/chemistry , Dianthus/genetics , Expressed Sequence Tags , Molecular Sequence Data , Plant Proteins/genetics , Plant Proteins/metabolism , Plant Roots/chemistry , Plant Roots/metabolism , Protein Precursors/metabolism , RNA, Plant/genetics , Ribosomes/metabolism , Saponaria/chemistry , Saponaria/genetics , Seeds/chemistry , Seeds/metabolism , Sequence Analysis, DNA
4.
Trends Plant Sci ; 12(4): 177-83, 2007 Apr.
Article in English | MEDLINE | ID: mdl-17360223

ABSTRACT

No clear consensus has emerged in the debate about the risks posed by transgenic crops and how to assess these risks accurately. In the meantime, interest is growing in strategies to impede transgene movement. This attention is being driven, in part, by expanding interest in using transgenic crops to produce pharmaceutical and industrial products. Potential strategies to impede transgene movement have been published in the scientific literature, and numerous patents have been submitted; however, the efficacy of such strategies has still to be evaluated in a field situation. In this review, we discuss some of the genetic strategies that could be used to restrict the spread of transgenes, although at present many of these technologies are still largely at a theoretical stage of development.


Subject(s)
Crops, Agricultural/genetics , Genetic Engineering/methods , Plants, Genetically Modified/physiology , Transgenes , Plants, Genetically Modified/growth & development , Reproduction/genetics , Reproduction/physiology , Risk Assessment
5.
Proc Natl Acad Sci U S A ; 100(11): 6855-9, 2003 May 27.
Article in English | MEDLINE | ID: mdl-12740441

ABSTRACT

We have developed a repressible seed-lethal (SL) system aimed at reducing the probability of transgene introgression into a population of sexually compatible plants. To evaluate the potential of this method, tobacco plants were transformed with an SL construct comprising gene 1 and gene 2 from Agrobacterium tumefaciens whereby gene 1 was controlled by the seed-specific phaseolin promoter modified to contain a binding site for the Escherichia coli TET repressor (R). The expression of this construct allows normal plant and seed development but inhibits seed germination. Plants containing the SL construct were crossed with plants containing the tet R gene to derive plant lines where the expression of the SL construct is repressed. Plant lines that contained both constructs allowed normal seed formation and germination, whereas seeds in which the SL construct was separated from the R gene through segregation did not germinate. The requirements of such a method to efficiently control the flow of novel traits among sexually compatible plants are discussed.


Subject(s)
Germination , Plants, Genetically Modified/embryology , Agrobacterium tumefaciens/genetics , Base Sequence , DNA Primers , Genotype , Phenotype , Plants, Genetically Modified/genetics , Plants, Genetically Modified/physiology , Polymerase Chain Reaction , Transformation, Genetic
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