1422528-33-3

Upstream product

• 57229-67-1 (S)-benzyl 2-((tert-butoxycarbonyl)amino)-3-(1H-indol-3-yl)propanoate 
• 820239-42-7 benzyl N-[(1S)-2-(1H-1,2,3-benzotriazol-1-yl)-1-methyl-2-oxoethyl]carbamate 
• 100-39-0 benzyl bromide 
• 13139-14-5 Boc-Trp-OH 

Downstream Products

• 1422528-42-4 β-Ala-L-Trp(Cbz-L-Ala)-OBn hydrogen chloride 
• 1422528-43-5 GABA-L-Trp(Z-L-Ala)-OBn hydrogen chloride 
• 1422528-37-7 C₃₁H₃₂N₄O₆ 
• 1422528-39-9 C₄₂H₄₃N₅O₉ 
• 1422528-44-6 C₃₂H₃₄N₄O₆ 
• 1422528-46-8 C₄₃H₄₅N₅O₉ 
• 1422528-45-7 C₃₃H₃₆N₄O₆ 
• 1422528-47-9 C₄₄H₄₇N₅O₉ 
• 1422528-34-4 L-Trp(Z-L-Ala)-OBn hydrogen chloride 
• 1422528-35-5 Boc-Gly-L-Trp(Z-L-Ala)-OBn 
• 1422528-40-2 Boc-β-Ala-L-Trp(Z-L-Ala)-OBn 
• 1422528-41-3 Boc-GABA-L-Trp(Cbz-L-Ala)-OBn 
• 1422528-36-6 Gly-L-Trp(Z-L-Ala)-OBn hydrogen chloride 

Relevant academic research and scientific papers

Long-range chemical ligation from N→N acyl migrations in tryptophan peptides via cyclic transition states of 10- to 18-members

Chemical ligations to form native peptides from N→N acyl migrations in Trp-containing peptides via 10- to 18-membered cyclic transition states are described. In this study, a statistical, predictive model that uses an extensive synthetic and computational approach to rationalize the chemical ligation is reported. N→N acyl migrations that form longer native peptides without the use of Cys/Ser/Tyr residues or an auxiliary group at the ligation site were achieved. The feasibility of these traceless chemical ligations is supported by the N-C bond distance in N-acyl isopeptides. The intramolecular nature of the chemical ligations is justified by using competitive experiments and theoretical calculations. Going the distance: Chemical ligations to form native peptides from N→N acyl migrations in Trp-containing peptides via 10- to 18-membered cyclic transition states are described (see scheme; Bn: benzyl; Z: benzyloxycarbonyl). The ligations are achieved without the use of Cys/Ser/Tyr residues or an auxiliary group. This new approach represents a significant development in the field.

Ligations of N-acyl tryptophan units to give native peptides via 7-, 10-, 11- and 12-membered cyclic transition states

N-Acyl tryptophan isopeptides undergo acyl transfer in chemical ligations via 7-, 10-, 11- and 12-membered cyclic transition states to yield natural peptides, representing the first examples of successful isopeptide ligations from N-acyl tryptophan units.