Peptides by Extension at the N‐ or C‐terminii of Lysine

Abstract

a and tripeptides 6a-e, (6b + 6b¢), (6e + 6e¢) incorporating Z -Lys were prepared in high yields (70-95%) and enantiopurity ( ‡97%) in partially aqueous acetonitrile solution by coupling using (

Chiral Acylation with N-(Protected α-Aminoacyl)benzotriazoles for Advantageous Syntheses of Peptides and Peptide Conjugates

“…[15][16][17][18][19][20] Apart from the development of solution-phase peptide synthesis, our methodology has also contributed to solid-phase peptide synthesis (SPPS) utilizing microwave irradiation.…”

“…Enantiopure dipeptides (LL and LD configuration) were obtained in 70-98% yield in high purity (>99%), without the use of chromatography (Scheme 4 and Table 2). 15,[17][18][19][20]38,39 Scheme 4 Preparation of dipeptides using N-(protected a-aminoacyl)benzotriazoles Cbz-L-Phe-L-Ala-OH 98 15 7…”

“…Cbz-DL-Ala-Cbz e -L-Lys-OH 88 18 73 N w -Cbz-L-Phe-Cbz a -L-Lys-OH 79 18 74 N w -Cbz-DL-Phe-Cbz a -L-Lys-OH 95 18 75 N w -Cbz-L-Trp-Cbz a -L-Lys-OH 93 18 76 N w -Fmoc-L-Met-Cbz a -L-Lys-OH 94 18 77…”

“…e -L-Lys Cbz-L-Ala-L-Trp-Cbz e -L-Lys-OH 7518 11 Cbz e -L-Lys Cbz-L-Phe-L-Met-Cbz e -L-Lys-OH 7218 12 Cbz e -L-Lys Cbz-L-Phe-DL-Met-Cbze-w -L-Lys Cbz-L-Ala-L-Trp-Cbz w -L-Lys-OH 7518 22Cbz w -L-Lys Cbz-L-Phe-L-Met-Cbz w -L-Lys-OH 72 18 23 Cbz w -L-Lys Cbz-L-Phe-DL-Met-Cbz w -L-Lys--w NO 2 -Arg Cbz-L-Asp(OBzl)-DL-Phe-L-w NO 2 -Arg-OH 82 38 a Isolated yield.…”

N‐Fmoc‐Protected(α‐Dipeptidoyl)Benzotriazoles for Efficient Solid‐Phase Peptide Synthesis by Segment Condensation

“…N ‐Protected( α ‐aminoacyl)benzotriazoles have been widely utilized for the preparation of chiral dipeptides (14–16) and 1,2,4‐oxadiazoles, a thiol esters (17) and as efficient coupling reagents for solid‐phase peptide synthesis (SPPS) (18). In this paper, we report segment condensation syntheses of five peptides from diverse N ‐Fmoc‐protected(α‐aminoacyl)benzotriazoles 1 and N ‐Fmoc‐protected(α‐dipeptidoyl)benzotriazoles 3 using mild microwave conditions.…”