Table 1. Synthesis of norbornapeptides (Scheme 1).
No. | Sequence a | mg | Yield b (%) | [M + H]+ calc./obs. c |
1 | l 1 Gk 2 fPE 1 a 2 | 34.9 | 82 | 725.40/725.40 |
2 | l1Gk2fPE1A2 | 25.9 | 60 | 725.40/725.40 |
3 | l1Gk2FPE1a2 | 11.4 | 56 | 725.40/725.40 |
4 | L 1Gk2fPE1a2 | 35.2 | 56 | 725.40/725.40 |
5 | l1Gk2FPE1A2 | 8.6 | 59 | 725.40/725.40 |
6 | L 1Gk2fPE1A2 | 22.4 | 61 | 725.40/725.40 |
7 | L 1Gk2FPE1a2 | 17.5 | 36 | 725.40/725.40 |
8 | L 1Gk2FPE1A2 | 34.3 | 81 | 725.40/725.40 |
9 | L 1GK2FPE1A2 | 6.6 | 27 | 725.40/725.40 |
10 | l1Gk2yPE1a2 | 8.9 | 4* | 741.39/741.39 |
11 | l1Gk2yPE1A2 | 10.9 | 59 | 741.39/741.42 |
12 | l1Gk2YPE1a2 | 4.7 | 37 | 741.39/741.42 |
13 | L 1Gk2yPE1a2 | 21.8 | 73 | 741.39/741.40 |
14 | l1Gk2YPE1A2 | 7.0 | 49 | 741.39/741.43 |
15 | L 1Gk2yPE1A2 | 20.5 | 42 | 741.39/741.39 |
16 | L 1Gk2YPE1a2 | 18.1 | 72 | 741.39/741.41 |
17 | L 1Gk2YPE1A2 | 7.3 | 15 | 741.39/741.45 |
18 | L 1GK2YPE1A2 | 13.8 | 37 | 741.39/741.40 |
19 | k 1Gk2fPE1a2 | 7.6 | 3* | 740.41/740.41 |
20 | l1Sk2fPE1a2 | 23.4 | 10* | 755.41/755.41 |
21 | l1Gk2fKE1a2 | 7.7 | 3* | 756.44/756.44 |
22 | k 1Gk2ePE1c2 | 7.4 | 3* | 754.36/754.36 |
23 | K 1Gk2fPE1A2 | 15.0 | 15* | 740.41/740.41 |
24 | L 1 S k 2fPE1A2 | 12.2 | 6* | 755.41/755.41 |
25 | L 1Gk2fKE1A2 | 12.0 | 5* | 756.44/756.44 |
26 | K 1Gk2ePE1C2 | 5.3 | 3* | 754.36/754.36 |
aOne-letter code for amino acids, upper case = l-, lower case = d-amino acids, sequences are given as prepared by SPPS written from N- to C-terminus, superscript numbers indicate residues involved in amide bond ring closures in 1st (1) and 2nd (2) cyclization.
bYields of HPLC purified products are given for the second cyclization reaction; asterisks mark total yields (SPPS and second cyclization). In all cases, yields are calculated for the corresponding trifluoroacetate salts.
cESI-MS spectra (positive mode) were recorded on a LTQ OrbitrapXL hybrid ion trap-Orbitrap mass spectrometer.