Table 3 Acylation of a series of Beltide-1 derivatives with 4-methoxy phenyl ester 18a

From: Selective N-terminal acylation of peptides and proteins with a Gly-His tag sequence

Peptide

N-Terminal mono-acylated product (%)

Di-acylated product (%)

Beltide-1 (13)

No reaction

No reaction

Ac-Beltide-1 (13-Ac)

No reaction

GHHH-Beltide-1 (14)

63

13

GHHHHHH-Beltide-1 (15)

92

8 (±1)

Ac-GHHHHHH-Beltide-1 (15Ac)

9 (±0.5)

GHHHHHHG-Beltide-1 (15G)

97

3 (±0.5)

GHHHHHHK-Beltide-1 (15K)

87

13 (±1)

Ac-GHHHHHHK-Beltide-1 (15K-Ac)

31 (±4)

  1. aConversion of a series of Beltide-1 derivatives after being treated at a concentration of 1 mM with 2.5 equiv. of 4-methoxy-phenyl ester 18 at 4 °C for 24 h as determined by LC–MS (UV, 215 nm). Standard deviations are based on duplicate measurements. Beltide-1 sequence DWLKAFYDKVAEKLKEAF, Lys underscored. The His acylation tags and compound numbers are indicated in bold