The deprotection of Lys(Mtt) revisited

Bourel-Bonnet, Line; Carion, Olivier; Gras‐Masse, Hélène; Melnyk, Oleg

doi:10.1002/1099-1387(200006)6:6<264::aid-psc248>3.0.co;2-a

Cited by 34 publications

(23 citation statements)

References 5 publications

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“…Furthermore, prolonged treatment with 2% TFA can result in cleavage of the peptide from the resin. 29 More significantly, adopting this improved strategy allows the initial synthesis of a fluorescein-preloaded Wang resin that can be used for the modular synthesis of diverse peptide scaffolds prepared in an analogous fashion to those reported herein.…”

Section: Discussionmentioning

confidence: 98%

Synthesis of fluorescein-labelled O-mannosylated peptides as components for synthetic vaccines: comparison of two synthetic strategies

et al. 2008

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Mannose-binding proteins on the surface of antigen-presenting cells (APCs) are capable of recognizing and internalizing foreign agents in the early stages of immune response. These receptors offer a potential target for synthetic vaccines, especially vaccines designed to stimulate T cells. We set out to synthesize a series of fluorescein-labelled O-mannosylated peptides using manual solid phase peptide synthesis (SPPS) on pre-loaded Wang resin, in order to test their ability to bind mannose receptors on human APCs in vitro. A flexible and reliable method for the synthesis of fluorescein-labelled O-mannosylated glycopeptides was desired in order to study their lectin-binding properties using flow cell cytometry. Two synthetic strategies were investigated: incorporation of a fluorescein label into the peptide chain via a lysine side chain epsilon-amino group at the final stage of standard Fmoc solid phase peptide synthesis or attachment of the fluorescein label to the N(alpha)-amino group of a lysine with further incorporation of a mannosylated peptide unit through the side chain N(epsilon)-amino group. The latter strategy proved more effective in that it facilitated SPPS by positioning the growing mannosylated peptide chain further removed from the fluorescein label.

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Section: Discussionmentioning

confidence: 98%

Synthesis of fluorescein-labelled O-mannosylated peptides as components for synthetic vaccines: comparison of two synthetic strategies

et al. 2008

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“…24 The side-chain Mtt group was removed by 1% TFA in DMF for 30 min. 25 After confirmation of removal of the Mtt…”

Section: Synthesis Of Compoundmentioning

confidence: 99%

Target-selective vesicle fusion system with pH-selectivity and responsiveness

et al. 2009

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“…A recent kinetic investigation of the N-Mtt cleavage reaction has been perfomed. 21 This work suggests that the kinetics of cleavage are slower than previously thought, in turn suggesting longer deprotection times are required. Short cleavage times were used in the synthesis, in order to reduce potential cleavage of the a-amino and side chain Boc protecting groups, which could result in cross-reaction.…”

Section: Structure-guided Design Of Cyclic Peptidesmentioning

confidence: 79%

Design, synthesis, biological activity and structural analysis of cyclic peptide inhibitors targeting the substrate recruitment site of cyclin-dependent kinase complexes

et al. 2004

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Inhibition of cyclin A- and cyclin E-associated cyclin-dependent kinase-2 (CDK2) activities is an effective way of selective induction of apoptotic cell death via the E2F pathway in tumour cells. The cyclin groove recognition motif (CRM) in the natural CDK-inhibitory (CDKI) tumour suppressor protein p27KIP1 was used as the basis for the design and synthesis of a series of cyclic peptides whose biological activity and structural characterisation by NMR and X-ray crystallography is reported. Whereas linear p27KIP1 sequence peptides were comparatively ineffective, introduction of side chain-to-tail constraints was found to be productive. An optimal macrocyclic ring size for the conformational constraint was determined, mimicking the intramolecular H-bonding system of p27. Molecular dynamics calculations of various macrocycles suggested a close correlation between ring flexibility and biological activity. Truncated inhibitor peptide analogues also confirmed the hypothesis that introduction of a cyclic conformational constraint is favourable in terms of affinity and potency. The structural basis for the potency increase in cyclic versus linear peptides was demonstrated through the determination and interpretation of X-ray crystal structures of complexes between CDK2/cylin A (CDK2A) and a constrained pentapeptide.

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The deprotection of Lys(Mtt) revisited

Cited by 34 publications

References 5 publications

Synthesis of fluorescein-labelled O-mannosylated peptides as components for synthetic vaccines: comparison of two synthetic strategies

Synthesis of fluorescein-labelled O-mannosylated peptides as components for synthetic vaccines: comparison of two synthetic strategies

Target-selective vesicle fusion system with pH-selectivity and responsiveness

Design, synthesis, biological activity and structural analysis of cyclic peptide inhibitors targeting the substrate recruitment site of cyclin-dependent kinase complexes

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