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. Author manuscript; available in PMC: 2013 Feb 28.
Published in final edited form as: J Am Chem Soc. 2012 Feb 15;134(8):3912–3916. doi: 10.1021/ja212182q

Table 2.

Selenoproline Ligation: Substrate Scope.a

graphic file with name nihms357578t9.jpg
Entry C-terminal
Peptide
Product Time / Yield
1 graphic file with name nihms357578t10.jpg H-ALLVNSSGPWEPLQ-OH
47
4.5 h, 84%
2 graphic file with name nihms357578t11.jpg H-ALLVNSSAPWEPLQ-OH
49
4.5 h, 88%
3 graphic file with name nihms357578t12.jpg H-ALLVNSSFPWEPLQ-OH
51
10 h, 80%
4 graphic file with name nihms357578t13.jpg H-ALLVNSSVPWEPLQ-OH
53
12 h, 66%
5 graphic file with name nihms357578t14.jpg H-ALLVNSSPPWEPLQ-OH
55
24 h, NR
a

Key: (a) MPAA, Ligation Buffer (6 M Gn•HCl, 200 mM NaH2PO4), pH 7.4–7.6, 23 °C; (b) DTT, Ligation Buffer; then TCEP, pH 5.0–6.0, 23 °C. P1: ALLVNSS−; P2: −WEPLQ.