Conventional and microwave‐assisted SPPS approach: a comparative synthesis of PTHrP(1–34)NH₂

Abstract

Attracted by the possibility to optimize time and yield of the synthesis of difficult peptide sequences by MW irradiation, we compared Fmoc/tBu MW-assisted SPPS of 1-34 N-terminal fragment of parathyroid hormone-related peptide (PTHrP) with its conventional SPPS carried out at RT. MWs were applied in both coupling and deprotection steps of SPPS protocol. During the stepwise elongation of the resin-bound peptide, monitoring was conducted by performing MW-assisted mini-cleavages and analyzing them by UPLC-ESI-MS. Identification of some deletion sequences was helpful to recognize critical couplings and as such helped to guide the introduction of MW irradiations to these stages.

Counter-ion effect on antistaphylococcal activity and cytotoxicity of selected antimicrobial peptides

“…Table 1 ) were synthesized manually by solid-phase method using Fmoc chemistry on the Rink amide or Wang resin (Fields and Noble 1990 ). All reactions were run using a CEM microwave synthesizer (Liberty Blue) to provide an enhanced efficiency as compared to that obtained by the conventional methodology (Rizzolo et al 2011 ). Coupling reaction was carried out by activation with DIC ( N,N’ -diisopropylcarbodiimide) in DMF ( N,N -dimethylformamide).…”

Antibodies from patients with rheumatoid arthritis target citrullinated histone 4 contained in neutrophils extracellular traps

“…Peptides were prepared on an automatic (APEX, AAPPTec) or on a microwave-assisted (Discover, CEM) synthesiser following the Fmoc/tBu solid-phase peptide strategy 26 27. Peptides were purified by high performance liquid chromatography (HPLC) (purity >95%) and characterised by electrospray ionisation-mass spectrometry (ESI-MS).…”

Modeling interaction between gp120 HIV protein and CCR5 receptor

“…The synthesis of the V3 loop peptide was performed starting from Fmoc‐Rink Amide resin (loading 0.12 mmol/g). The peptide fragment SLGPGRVWYTTGQIVGDIRKAHC‐Rink Amide resin was synthesized by microwave‐assisted solid‐phase peptide synthesis using a Liberty Blue‐automated microwave peptide synthesizer (CEM Corporation, Matthews, NC, USA) and following the protocol described elsewhere . The remaining amino acids (GCTRPNNNTRKRV) were coupled manually using the corresponding Fmoc‐protected amino acids (5 equiv), HATU (5 equiv), and DIPEA (7 equiv) for 50 min at room temperature till the completion of the peptide sequence.…”