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. 2015 Jul 13;6(10):5473–5490. doi: 10.1039/c5sc01699a

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.