Biomaterial Database

Environmentally Sensible Organocatalytic Fmoc/t-Bu Solid-Phase Peptide Synthesis. 2022

Jan Pawlas, and Jon H Rasmussen

PolyPeptide Group, Limhamnsvägen 108, P.O. Box 30089, 20061 Limhamn, Sweden.

Despite numerous reports on catalytic amide bond formation (ABF), these methods have thus far had a minimal impact on the universal fluorenylmethoxycarbonyl (Fmoc)/t-Bu solid-phase peptide synthesis (SPPS) methodology. We now report a proof-of-principle Fmoc/t-Bu SPPS in which both couplings and Fmoc deprotections were catalyzed by readily available reagents in an inexpensive green solvent. Couplings were carried out with >99% stereoselectivity, employing 1.1 equiv of Fmoc amino acids (AAs), using diisopropylcarbodiimide (DIC) as a coupling agent and 1-hydroxy-1,2,3-triazole-5-carboxylic acid ethyl ester (HOCt) (TON ∼ 30) as a catalyst, while Fmoc deprotections were carried out using 1,8-diazabicyclo(5.4.0)undec-7-ene (DBU) (TON ∼ 7), facilitating synthesis of a model pentapeptide in 95% HPLC purity while also enabling minimization of solvent washing.

UI	MeSH Term	Description	Entries
D010455	Peptides	Members of the class of compounds composed of AMINO ACIDS joined together by peptide bonds between adjacent amino acids into linear, branched or cyclical structures. OLIGOPEPTIDES are composed of approximately 2-12 amino acids. Polypeptides are composed of approximately 13 or more amino acids. PROTEINS are considered to be larger versions of peptides that can form into complex structures such as ENZYMES and RECEPTORS.	Peptide,Polypeptide,Polypeptides
D005449	Fluorenes	A family of diphenylenemethane derivatives.
D000596	Amino Acids	Organic compounds that generally contain an amino (-NH2) and a carboxyl (-COOH) group. Twenty alpha-amino acids are the subunits which are polymerized to form proteins.	Amino Acid,Acid, Amino,Acids, Amino
D012997	Solvents	Liquids that dissolve other substances (solutes), generally solids, without any change in chemical composition, as, water containing sugar. (Grant & Hackh's Chemical Dictionary, 5th ed)	Solvent
D060327	Solid-Phase Synthesis Techniques	Techniques used to synthesize chemicals using molecular substrates that are bound to a solid surface. Typically a series of reactions are conducted on the bound substrate that results in either the covalent attachment of specific moieties or the modification of existing function groups. These techniques offer an advantage to those involving solution reactions in that the substrate compound does not have to be isolated and purified between the reaction steps.	Solid-Phase Synthesis,Peptide Synthesis, Solid-Phase,Solid-Phase Nucleotide Synthesis,Solid-Phase Nucleotide Synthesis Techniques,Solid-Phase Peptide Synthesis,Solid-Phase Peptide Synthesis Techniques,Solid-Phase Synthesis Methods,Synthesis, Solid-Phase,Method, Solid-Phase Synthesis,Methods, Solid-Phase Synthesis,Nucleotide Syntheses, Solid-Phase,Nucleotide Synthesis, Solid-Phase,Peptide Syntheses, Solid-Phase,Peptide Synthesis, Solid Phase,Solid Phase Nucleotide Synthesis,Solid Phase Nucleotide Synthesis Techniques,Solid Phase Peptide Synthesis,Solid Phase Peptide Synthesis Techniques,Solid Phase Synthesis,Solid Phase Synthesis Methods,Solid Phase Synthesis Techniques,Solid-Phase Nucleotide Syntheses,Solid-Phase Peptide Syntheses,Solid-Phase Syntheses,Solid-Phase Synthesis Method,Solid-Phase Synthesis Technique,Syntheses, Solid-Phase,Syntheses, Solid-Phase Nucleotide,Syntheses, Solid-Phase Peptide,Synthesis Method, Solid-Phase,Synthesis Methods, Solid-Phase,Synthesis Technique, Solid-Phase,Synthesis Techniques, Solid-Phase,Synthesis, Solid Phase,Synthesis, Solid-Phase Nucleotide,Synthesis, Solid-Phase Peptide,Technique, Solid-Phase Synthesis,Techniques, Solid-Phase Synthesis