Table. 1 Initial investigation of the model reactiona

From: Orthogonal bioconjugation targeting cysteine-containing peptides and proteins using alkyl thianthrenium salts

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Entry

Organic solvent

Buffer

v/v

Yield (%)b

1

DMSO

PB buffer (pH 8.0, 0.2 M)

1:1

54

2

THF

PB buffer (pH 8.0, 0.2 M)

1:1

13

3

DMF

PB buffer (pH 8.0, 0.2 M)

1:1

48

4

MeCN

PB buffer (pH 8.0, 0.2 M)

1:1

16

5

MeOH

PB buffer (pH 8.0, 0.2 M)

1:1

46

6

2-MeTHF

PB buffer (pH 8.0, 0.2 M)

1:1

<5

7

DMSO

PB buffer (pH 6.5, 0.5 M)

1:1

62

8

DMSO

PB buffer (pH 7.0, 0.2 M)

1:1

<5

9

DMSO

PB buffer (pH 9.0, 0.2 M)

1:1

53

10

DMSO

PBS buffer (pH 7.0, 0.2 M)

1:1

38

11

DMSO

PBS buffer (pH 8.0, 0.2 M)

1:1

<5

12

DMSO

PBS buffer (pH 9.0, 0.2 M)

1:1

<5

13

DMSO

Tris-HCl buffer (pH 7.0, 1.0 M)

1:1

28

14

DMSO

Tris-HCl buffer (pH 8.0, 1.0 M)

1:1

58

15c

DMSO

Tris-HCl buffer (pH 9.0, 1.0 M)

1:1

63

16d

DMSO

TE buffer (pH 7.0, 10×)

1:1

<5

17

DMSO

TE buffer (pH 8.0, 10×)

1:1

<5

18

DMSO

Tris-HCl buffer (pH 9.0, 1.0 M)

3:1

87

19

DMSO

Tris-HCl buffer (pH 9.0, 1.0 M)

1:3

58

  1. aUnless otherwise stated, the reaction was carried out with 0.1 mmol 1a and 0.1 mmol 2a in 2 mL solvent at room temperature.
  2. bIsolated yield after semipreparative HPLC was given.
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