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. 2021 Mar 8;60(16):9022–9031. doi: 10.1002/anie.202014511

Table 3.

Cys–Lys stapling in presence of additional ivDde protected and unprotected Lys. Inline graphic

 

X=

graphic file with name ANIE-60-9022-g002.jpg

 

graphic file with name ANIE-60-9022-g023.jpg

Peptide

Entry

Rel. abs. [%][c]

Entry

Rel. abs. [%]

A

 

 

 

 

Ac‐YGGEAARK(ivDde)ACAREKAARE‐NH2

1

117 %

(ivDde‐26 a′)

97 %[d] (26 a′)

2

72 %

(ivDde‐26 a′′)

0 % (26 a′′)

(ivDde‐26 a)

B

 

 

 

 

Ac‐YGGEAARKACAREKAARE‐NH2 (26 a)

3

92 % (26 a′)

6

74 % (26 a′′)

Ac‐YGGEKAREACAREKAARE‐NH2 (26 b)

4

91 % (26 b′)

–

–

Ac‐YGGEAAREACAREKAAREK‐NH2 (26 c)

5

95 % (26 c′)

–

–

[a] Reaction conditions: 9 (1.1 equiv), DIPEA (2.5 equiv), 1 mM, 37 °C, 30 min. [b] Reaction conditions: 35 wt % hydrazine in water, 2 %, 37 °C, 30 min. [c] Relative absorbance of stapled product compared to a standard solution of starting material at 210 nm. [d] Relative absorbance of stapled product compared to a standard solution of 26 a at 210 nm.