2017
DOI: 10.1039/c7cc06550g
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Bypassing the proline/thiazoline requirement of the macrocyclase PatG

Abstract: Macrocyclisation of fully non-peptidic compounds and non-heterocycle containing macrocycles using the peptidic ligase PatGmac.

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Cited by 26 publications
(29 citation statements)
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“…Even so, PatG accepts substrates with proline substituting for thiazoline, as well as triazoles and, interestingly, heterocycles comprised of disulfide linked cysteine-cysteine (e.g., CC-SYD, etc.) (Oueis et al, 2016; Oueis, Stevenson, et al, 2017). These are synthetically useful alternatives in the creation of large molecules.…”
Section: Proteasesmentioning
confidence: 99%
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“…Even so, PatG accepts substrates with proline substituting for thiazoline, as well as triazoles and, interestingly, heterocycles comprised of disulfide linked cysteine-cysteine (e.g., CC-SYD, etc.) (Oueis et al, 2016; Oueis, Stevenson, et al, 2017). These are synthetically useful alternatives in the creation of large molecules.…”
Section: Proteasesmentioning
confidence: 99%
“…The minimal substrate requirement for macrocyclization by PatG (i.e. minimal three residue follower sequence preceded by a heterocycle) has prompted several efforts focused on utilizing the isolated protease domain as a biotechnology tool (Alexandru-Crivac et al, 2017; McIntosh, Robertson, et al, 2010; Oueis et al, 2016; Oueis, Nardone, et al, 2017; Oueis, Stevenson, et al, 2017; Sardar, Lin, et al, 2015). For example, the macrocyclase was predicted to be useful in producing discrete compounds such as peptides that mimic hormones or neuropeptides, or libraries of natural unnatural products.…”
Section: Proteasesmentioning
confidence: 99%
See 2 more Smart Citations
“…While proline and other heterocycles in artificial substrates is sometimes accepted by PatG, the reaction is usually much slower than it is with azoline. [30][31] Generally, azolines are installed by a specific cyanobactin heterocyclase enzyme prior to macrocyclization. 32 Although the heterocycle provides rigidity to the backbone to assist macrocyclization, this additional biochemical step increases complexity and compromises the yield for downstream applications such as library generation.…”
Section: Introductionmentioning
confidence: 99%