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. Author manuscript; available in PMC: 2011 Dec 1.
Published in final edited form as: J Am Chem Soc. 2010 Nov 4;132(47):17045–17051. doi: 10.1021/ja1084628

Table 3.

HOBT-Mediated Peptide Coupling.a

graphic file with name nihms250720t15.jpg
peptide 1
peptide 2		 product yield L/D
ratio
1 Boc-VF-COSH 21
H2N-F-OtBu 22 		graphic file with name nihms250720t16.jpg 89%a 97:3
2 Boc-AFGF-COSH 24
H2N-VPVWAG 13 		graphic file with name nihms250720t17.jpg 82%b 94:6
3 Boc-AFGA-COSH 26
H2N-VPVWAG 13 		graphic file with name nihms250720t18.jpg 80% 97:3
4 Ac-GRFSWGA-COSH 28
H2N-VPVWAG 13 		graphic file with name nihms250720t19.jpg 82%c >99:1
5 Ac-GRFSWGA-COSH 28
H2N-FGPELWP 8 		graphic file with name nihms250720t20.jpg 82% >99:1
6 Ac-GRFSWGL-COSH 31
H2N-VPVWAG 13 		graphic file with name nihms250720t21.jpg 80% 96:4
7 Ac-GRFSWGV-COSH 33
H2N-VPVWAG 13 		graphic file with name nihms250720t22.jpg 86%b 95:5
a

Key: general procedure, DMSO, 2 eq HOBT, 4Å MS, rt, 12h;

(a)

CH2Cl2, 2 eq HOBT, 4Å MS, rt, 12h;

(b)

DMSO, 2 eq HOOBT, 4Å MS, rt, 12h;

(c)

DMSO, 0.3 eq HOBT, 4Å MS, rt, 20h. HOOBT: hydroxy-3,4-dihydro-4-oxo-1,2,3-benzotriazine.