Communications Chemistry

Table 3 Investigation of the scope of isoxazoliniums^a

From: Chemoselective and photocleavable cysteine modification of peptides and proteins using isoxazoliniums


Entry	Isoxazolinium reagents	Modified peptides	Conversions (%)^b
1	2a	3a	96
2	2b	3a	87
3	2c	3a, 3aa	31, 21
4	2d	3a, 3aa	27, 20
5	2e	3a	>99
6	2f	3a	98
7	2g	3a, 3ab	61, 27
8	2h	3ac	98
9	2i	3b	97
10	2j	3c	98
13	2k	3d	97
14	2l	3e	97
15	2m	3f	99
16	2n	3g	98
17	2o	3h	99
18	2p	3i	97
19	2q	3j	98

^aConditions of the modifications: treatment of STSSSCNLSK 1a (0.1 mM) with isoxazolinium reagent 2a–q (1 equivalent with 5 mol% of AgNO₃) in 50 mM pH 7.4 PBS buffer/CH₃CN (19:1) at 25 °C for 2 h. ^bConversion of the modification was determined by LC-MS analysis

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