Branched peptides, synthesis

BW Erickson, RB Merrifield. Use of chlorinated benzyloxycarbonyl protecting groups to eliminate Ne-branching at lysine during solid-phase peptide synthesis. J Am Chem Soc 95, 3757, 1973. 

BW Bycroft, WC Chan, SR Chhabra, ND Hone. A novel lysine-protecting procedure for continous flow solid phase synthesis of branched peptides. (Dde group) J Chem Soc Chem Commun 778, 1993. 

Carbohydrates and polysaccharides, on the one hand, and peptides and proteins, on the other, have been considered as separate classes of natural products for a long time. Fundamental chemical methodology for the synthesis of both saccharides and peptides was developed by Emil Fischer et al. at the beginning of the 20th century. 1,2 However, the harsh conditions employed in early solution and solid-phase peptide synthesis hindered the combination of peptide and carbohydrate chemistry, i.e. glycopeptide synthesis. Considerable efforts were made to combine the two branches of natural product chemistry, and the state of the art within glycopeptide synthesis has improved dramatically during the last decades, as described in a number of reviews. 3 23,512"514 ... 

The Nervous System Research branch of Novartis Pharma Ltd in Basel, Switzerland, and the University of Hull investigated peptide synthesis in chip-based microreactors... 

Synthesis of Linear and Branched Peptides by Alfyl-Based Protection... 

Scheme 6 Synthesis of a Branched Peptide by Allyl-Based Protection ...

Three l-(2-nitrophenyl)ethyl phosphoroamino acid building blocks (68), (69) and (70) for solid-phase peptide synthesis have been described (Figure 17). A new straightforward method of synthesis of dendrimers, using two branched monomers (CA2 and DB2) has been desribed (Figure 18). ... 

The synthesis of branched peptides using masked side-chain thioester derivatives of Asp and Glu which are compatible with Fmoc-SPPS is an important goal. Boll et al. synthesized cyclic and branched chain peptides using bis (2-sulfanylethyl)amido (SEA) side-chain derivatives of Asp and Glu via Fmoc SPPS [77]. The tail-to-side-chain cyclization via an in situ reduction of both acyclic and cyclic disulfides with tris(2-carboxyethyl)phosphine (TCEP) triggered the SEA intramolecular ligation. Glu derivatives cyclized more readily than the Asp analogues and without formation of side products (Scheme 9). 

The Nervous System Research branch of Novartis Pharma Ltd in Basel, Switzerland, and the University of Hull investigated peptide synthesis in chip-based microreactors [5]. P-Amino adds were chosen for demonstrating feasibility of microreactor processing, as there are no chiral centers that may complicate the analysis of the products [6]. 

Orthogonal amine-protecting groups for the solid phase synthesis of branched peptides... 

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