On‐Surface Cyclization of Tetrapeptides Using Molecularly Imprinted Polymers as Non‐Covalent Auxiliaries

Lin, Yee-Fung; Lee, Shih-Ming; Chen, Chi-Tai; Lu, Kao-Haw; Tai, Dar-Fu

doi:10.1002/jccs.200900018

Cited by 5 publications

(4 citation statements)

References 27 publications

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“…This may rightly be deemed a daunting task. Nonetheless, MIP‐based catalytic systems and the use of MIPs in synthesis continue to evolve . Recent reports of several systems with significant catalytic power bodes well for the continued development in this sector.…”

Section: Applicationsmentioning

confidence: 99%

Molecular imprinting science and technology: a survey of the literature for the years 2004-2011

2014

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SummaryHerein we present a survey of the literature covering the development of molecular imprinting science and technology over the years 2004 to 2011. In total, 3779 references to the original papers, reviews, edited volumes and monographs from this period are included, along with recently identified uncited materials from prior to 2004 which were omitted in the first instalment of this series covering the years 1930 to 2003. 1 In the presentation of the assembled references, a section presenting reviews and monographs covering the area is followed by sections describing fundamental aspects of molecular imprinting including the development of novel polymer formats. Thereafter, literature describing efforts to apply these polymeric materials to a range of application areas is presented. Current trends and areas of rapid development are discussed.2

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Section: Applicationsmentioning

confidence: 99%

Molecular imprinting science and technology: a survey of the literature for the years 2004-2011

2014

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“…We focused our efforts using CtetPs as β-turn (U-ACPs) mimicry as innate defense regulators (IDRs) to explore novel antitumor activities. The difficult macrocyclizations for synthesizing hydrophobic CtetPs and their side-chain protected peptides was a challenging task [ 38 , 39 ]. In view of the wide array of bioactivities possessed by natural CtetPs, an efficient large-scale synthesis of pure products is required to evaluate the biological potential of promising bioactive compounds.…”

Section: Resultsmentioning

confidence: 99%

Antitumor and Antimicrobial Activity of Some Cyclic Tetrapeptides and Tripeptides Derived from Marine Bacteria

et al. 2015

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Marine derived cyclo(Gly-l-Ser-l-Pro-l-Glu) was selected as a lead to evaluate antitumor-antibiotic activity. Histidine was chosen to replace the serine residue to form cyclo(Gly-l-His-l-Pro-l-Glu). Cyclic tetrapeptides (CtetPs) were then synthesized using a solution phase method, and subjected to antitumor and antibiotic assays. The benzyl group protected CtetPs derivatives, showed better activity against antibiotic-resistant Staphylococcus aureus in the range of 60–120 μM. Benzyl group protected CtetPs 3 and 4, exhibited antitumor activity against several cell lines at a concentration of 80–108 μM. However, shortening the size of the ring to the cyclic tripeptide (CtriP) scaffold, cyclo(Gly-l-Ser-l-Pro), cyclo(Ser-l-Pro-l-Glu) and their analogues showed no antibiotic or antitumor activity. This phenomenon can be explained from their backbone structures.

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“…44 Cyclic tetrapeptide c(Pro-Phe-Pro-Phe) was also prepared in the chemical laboratory by surface cyclization of a linear tetrapeptide using molecularly printed polymers. 45 In both articles, the product was analyzed using standard approaches. In our article we show few hidden features of this system; structural complexity in function of chirality.…”

Section: Introductionmentioning

confidence: 99%

Influence of heterochirality on the structure, dynamics, biological properties of cyclic(PFPF) tetrapeptides obtained by solvent-free ball mill mechanosynthesis

Potrzebowski,

Kazmierski,

Wielgus

et al. 2024

Preprint

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Cyclic tetrapeptides c(Pro-Phe-Pro-Phe) obtained by the mechanosynthetic method using a ball mill were isolated in a pure stereochemical form as a homochiral system (all L-amino acids, sample A) and as a heterochiral system with D configuration at one of the stereogenic centers of Phe (sample B). The structure and stereochemistry of both samples were determined by X-ray diffraction studies of single crystals. In DMSO and acetonitrile, sample A exists as an equimolar mixture of two conformers, while only one is monitored for sample B. The conformational space and energetic preferences for possible conformers were calculated using DFT methods. The distinctly different conformational flexibility of the two samples was experimentally proven by Variable Temperature (VT) and 2D EXSY NMR measurements. Both samples were docked to histone deacetylase HDAC8. Cytotoxic studies proved that none of the tested cyclic peptide is toxic.

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On‐Surface Cyclization of Tetrapeptides Using Molecularly Imprinted Polymers as Non‐Covalent Auxiliaries

Cited by 5 publications

References 27 publications

Molecular imprinting science and technology: a survey of the literature for the years 2004-2011

Molecular imprinting science and technology: a survey of the literature for the years 2004-2011

Antitumor and Antimicrobial Activity of Some Cyclic Tetrapeptides and Tripeptides Derived from Marine Bacteria

Influence of heterochirality on the structure, dynamics, biological properties of cyclic(PFPF) tetrapeptides obtained by solvent-free ball mill mechanosynthesis

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