To Rink or Not to Rink Amide Link, that is the Question to Address for More Economical and Environmentally Sound Solid-Phase Peptide Synthesis

Evaluation of COMU as a coupling reagent for in situ neutralization Boc solid phase peptide synthesis

“…In addition to the polystyrene-based resins, we included the PEG-based resin, ChemMatrixW. This resin type demonstrates excellent swelling properties in a range of solvents and has been shown to improve crude purities with both Fmoc-chemistry and Boc-chemistry [38][39][40][41][42].…”

Methods for the Peptide Synthesis and Analysis

“…In comparative studies among several resins on the synthesis of human stromal cell-derived factor (SDF)-1α [24] and the acyl carrier protein (ACP [65][66][67][68][69][70][71][72][73][74] [25], higher purities were obtained with CM than with PS supports when using similar loadings. Compatibility of all these PEG-based resins with aqueous buffers allows their use for biochemical applications such as on-resin screening of chemical libraries and the development of affinity chromatography [26][27][28][29].…”

“…Asn and Gln are usually being used without protection. The Lys side-chain is usually protected with the benzyloxycarbonyl (Cbz, Z) (23) or the 2-chlorobenzyloxycarbonyl (2-Cl-Z) group and for His/Arg, the p-toluenesulfonyl (Tos) (22) His, another option is to employ the 2,4-dinitrophenyl group (Dnp) (25), which is removed by thiolysis prior to the HF cleavage step. The Alloc (17) and (1-(4,4-dimethyl-2,6-dioxocylohex-1-ylidene)-3-ethyl) (Dde) (26) group, which is removed by hydrazine, introduce an extra degree of orthogonality, and are used as side-chain protecting groups for Lys to access cyclic and branched peptides.…”

Peptides As Therapeutics with Enhanced Bioactivity

“…CM was very stabile with a high loading capacity and has been used in both aqueous solutions and during the synthesis of difficult hydrophobic peptides [21]. Kessam et al suggested that a newly developed resin incorporating PEG polymerized onto a poly(vinyl alcohol) core may be even more valuable, economically and environmentally, after demonstrating its promise against other resins in synthesis of a section of acyl carrier protein [23]. Kessam et al suggested that a newly developed resin incorporating PEG polymerized onto a poly(vinyl alcohol) core may be even more valuable, economically and environmentally, after demonstrating its promise against other resins in synthesis of a section of acyl carrier protein [23].…”