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. Author manuscript; available in PMC: 2016 Apr 5.
Published in final edited form as: J Pept Sci. 2016 Mar;22(3):186–191. doi: 10.1002/psc.2859

Table 2.

Syntheses of N-acyl-peptides using DPGOx 3 and NaHCO3 in DMF.

graphic file with name nihms-749321-t0002.jpg

entry N-protected
α-amino acid		 C-protected
α-amino acid		 conditionsa time
(h)		 product yield
(%)		 de
(%)
[1+1]
1 Ac-L-Phe-OH HCl•H-L-Ala-OMe A 2 Ac-L-Phe-L-Ala-OMe 85 >99b
2 Ac-L-Tyr-OH HCl•H-L-Ala-OMe A 2 Ac-L-Tyr-L-Ala-OMe 75 >99b
3 Ac-L-Tyr-OH HCl•H-L-Ala-NH2 B 2 Ac-L-Tyr-L-Ala-OMe 95 >92c
4 Ac-L-Ser-OH HCl•H-L-Ala-OMe A 2 Ac-L-Ser-L-Ala-OMe 85 >99b
5 CHO-L-Leu-OH HCl•H-L-Ala-OMe A 3 CHO-L-Leu-L-Ala-OMe 70 >99b
6 CHO-L-Leu-OH HCl•H-L-Ala-OMe B 3 CHO-L-Leu-L-Ala-OMe 95 >99b
7 CHO-L-Phe-OH HCl•H-L-Ala-OMe A 3 CHO-L-Phe-L-Ala-OMe 73 >99b
8 CHO-L-Phe-OH HCl•H-L-Ala-OMe B 3 CHO-L-Phe-L-Ala-OMe 95 >99b
[4+1]
9 Ac-L-Lys(Z)-OH HCl•H-L-Ala-L-Lys(Z)-L-Lys(Z)-L-Phe-OMe A 2 Ac-L-Lys(Z)-L-Ala-L-Lys(Z)-Lys(Z)-L-Phe-OMe 80 >92c
10 CHO-L-Lys(Z)-OH HCl•H-L-Ala-L-Lys(Z)-L-Lys(Z)-L-Phe-OMe A 2 CHO-L-Lys(Z)-L-Ala-L-Lys(Z)-L-Lys(Z)-L-Phe-OMe 81 >92c
[5+1]
11 Ac-L-Lys(Z)-OH HCl•H-L-Lys(Z)-L-Ala-L-Lys(Z)-L-Lys(Z)-L-Phe-OMe A 3 Ac-L-Lys(Z)-L-Lys(Z)-L-Ala-L-Lys(Z)-L-Lys(Z)-L-Phe-OMe 80 >92c
12 CHO-L-Lys(Z)-OH HCl•H-L-Lys(Z)-L-Ala-L-Lys(Z)-L-Lys(Z)-L-Phe-OMe A 3 CHO-L-Lys(Z)-L-Lys(Z)-L-Ala-L-Lys(Z)-L-Lys(Z)-L-Phe-OMe 80 >92c
a

A: N-acyl-α-amino acid (1.5 equiv), C-protected α-amino acid (1.0 eqiv), 3 (1.5–2.0 equiv), NaHCO3 (3 equiv), DMF (0.2 M); B: N-acyl-α-amino acid (3.0 equiv), C-protected α-amino acid (1.0 eqiv), 3 (3.0 equiv), NaHCO3 (3 equiv), DMF (0.2 M);

b

de was determined by HPLC;

c

de was determined by 1H-NMR analysis;