Search results for "Solid-phase synthesis"

Stereocontrolled solid-phase synthesis of fluorinated partially-modified retropeptides via tandem aza-Michael/enolate-protonation

2003

N-Acylation of Wang resin-bound l-α-amino acids with 2-trifluoromethyl-propenoyl chloride, followed by asymmetric tandem aza-Michael/enolate-protonation by a series of l-α-amino esters and final release from the resin, afforded a representative library of partially-modified retropeptides incorporating a stereodefined trifluoroalanine surrogate. The stereocontrol can be dramatically improved (up to 15:1) by using apolar solvents like carbon tetrachloride and DABCO as base.

Carbohydrates as Polyfunctional Scaffolds in Combinatorial Synthesis

2006

Carbohydrates are inexpensive, polyfunctional molecules which contain a high density of stereogenic centers. Taking advantage of these particular properties monosaccharides like glucose or mannose have been used for the construction of peptidomimetics which simulate recognition sites of somatostatin or RGD ligands of integrins. Due to their poly functionality, carbohydrates are considered promising scaffolds for combinatorial syntheses either in solution or on solid phase. The application of carbohydrate scaffolds, however, requires sets of orthogonally stable, selectively removable protecting groups, and the challenge in this combinatorial strategy increases with increasing number of hydro…

Solid-Phase Synthesis of Oligo(p-benzamide) Foldamers

2006

[reaction: see text] A coupling protocol has been developed which allows the synthesis of oligo(p-benzamide)s on solid support. Aromatic carboxylic acids are activated in situ with thionyl chloride and used to acylate secondary aromatic amines. N-p-Methoxy benzyl (PMB) as well as N-hexyl protected monomers were investigated. Heterosequences of both monomers were synthesized. Such nanoscale objects are important building blocks for supramolecular chemistry.

Solid-Phase Synthesis of Biologically Important Glycopeptides

2003

New Perspectives in Polymer-Supported Peptide Synthesis

1982

The (2-Phenyl-2-trimethylsilyl)ethyl(PTMSEL) Linker—A Novel Linker for the Solid-Phase Synthesis of Protected Peptides and Glycopeptides Cleavable wi…

2002

A facile cleavage of allyl ethers on solid phase

2000

Abstract A simple and efficient protocol for the cleavage of allyl ethers on solid phase using a palladium(0)-catalyzed allyl transfer reaction is reported.

Receptor-mediated uptake of boron-rich neuropeptide y analogues for boron neutron capture therapy.

2014

Peptidic ligands selectively targeting distinct G protein-coupled receptors that are highly expressed in tumor tissue represent a promising approach in drug delivery. Receptor-preferring analogues of neuropeptide Y (NPY) bind and activate the human Y1 receptor subtype (hY1 receptor), which is found in 90% of breast cancer tissue and in all breast-cancer-derived metastases. Herein, novel highly boron-loaded Y1 -receptor-preferring peptide analogues are described as smart shuttle systems for carbaboranes as (10) B-containing moieties. Various positions in the peptide were screened for their susceptibility to carbaborane modification, and the most promising positions were chosen to create a mu…

Modular Solid-Phase Synthesis of Antiprotozoal Barnesin Derivatives

2020

Here, we applied and optimized a solid support (SP)-based Horner-Wadsworth-Emmons reagent to prepare SP-bound vinylogous amino acids. Subsequent SP-based peptide synthesis, global deprotection, and chemical modifications yielded 14 lipodipeptides carrying vinylogous amino acids, including the natural product barnesin A (1). Biological evaluation revealed that several synthesized derivatives show micromolar to nanomolar inhibitory activity against papain-like cysteine proteases, human cathepsin L, and rhodesain.

Synthesis and Biological Evaluation of a Multiantigenic Tn/TF-Containing Glycopeptide Mimic of the Tumor-Related MUC1 Glycoprotein

2006