Benzotriazole-Assisted Solid-Phase Assembly of Leu-Enkephalin, Amyloid β segment 34−42, and other “Difficult” Peptide Sequences

Abstract

Microwave-assisted solid-phase syntheses of six "difficult" peptides, H-VVSVV-NH(2) (3), H-VVVSVV-NH(2) (4), H-VIVIG-OH (5), H-TVTVTV-NH(2) (6), H-VKDGYI-NH(2) (7), and H-VKDVYI-NH(2) (8), were achieved utilizing N-(Fmoc-alpha-aminoacyl)benzotriazoles. Extension to the syntheses of Leu-enkephalin (9) and amyloid-beta (34-42) (10) demonstrates that this strategy comprises an efficient route to new and known "difficult" peptides.

Total synthesis and antimicrobial evaluation of natural albomycins against clinical pathogens

“…Failure to optimize the condition after numerous efforts prompted us to explore an alternative strategy. Fortunately, under active amide-mediated coupling conditions developed by Katritzky 28–31 , tripeptide 4 could be obtained in an iterative fashion from 11 in 77% yield over two steps without any detectable epimerization. Tripeptide 4 was condensed with L-serine tert -butyl ester hydrochloride in the presence of HATU and DIPEA to generate tert -butyl ester 13 in 95% yield.…”

Synthesis, characterization, crystal structure and DFT studies on 3-(1H-benzo[d][1,2,3]triazol-1-yl)-1-oxo-1-m-tolylpropan-2-yl-nicotinate

“…Also, benzotriazoles are extensively used as synthetic auxiliaries in organic chemistry [5][6][7] and versatile ligands in coordination chemistry [8,9]. For example, the deprotonated benzotriazolate anion can coordinate up to three metal centres via its three nitrogen donors [10,11] and the copper complexes of benzotriazole drew many attentions due to the importance of benzotriazole as a corrosion inhibitor [12,13].…”

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

“…The introduction in 1992 of MW irradiation in peptide chemistry stimulated a host of interest followed by numerous efforts to use it to overcome synthetic difficulties resulting in sluggish reactions, low yields and complex reaction crude products that were hard to purify1. During the last decade the growing interest in MW field has been marked by the progress in developing scientific MW equipment to embrace specific research needs2–5. In general, introduction of MW technology led to the shortening of reaction time that resulted in higher purity of crudes and increased yields of the pure final product.…”