Solid-phase synthesis of C-terminally modified ... - ResearchGate

C-TERMINALLY MODIFIED PEPTIDES 691
(75%). Crude yield (50%). Maldi-Tof; Mass calculated: 990.7
(M + Na) + ; measured: 990.3 (M + Na) + .
C 17 H 35 CO-Ala-Gly-Ala-Gly-Lys-Gly-Ala-Gly-Ala-Gly-
NHC 18 H 37 (20). The compound was prepared analogously to
1. Resin loading: 0.68 mmol g −1 (99%). Crude yield (54%).
Maldi-Tof; Mass calculated: 1256.8 (M + Na) + ; measured:
1256.5 (M + Na) + .
C 17 H 35 CO-Ala-Gly-Ala-Gly-Glu-Gly-Ala-Gly-Ala-Gly-
NHC 18 H 37 (21). The compound was prepared analogously to
1. Resin loading: 0.68 mmol g −1 (99%). Crude yield (52%).
Maldi-Tof; Mass calculated: 1255.9 (M + Na) + ; measured:
1255.5 (M + Na) + .
Ac-Gly-Ala-Asn-Pro-Asn-Ala-Ala-Gly-NH(CH 2 ) 3 -N 3
(22). The compound was prepared analogously to 1. Resin
loading: 0.55 mmol g −1 (99%). Crude yield (75%). ESI-ion
trap; Mass calculated (M + Na) + : 817.4; measured: 817.4
(M + Na) + .
C 15 H 31 -Gly-Ala-Asn-Pro-Asn-Ala-Ala-Gly-NH(CH 2 ) 3 -N 3
(23). The compound was prepared analogously to 1, using
3-amino-propylazide. Resin loading: 0.55 mmol g −1 (99%).
Isolated yield (40%). Maldi-Tof; Mass calculated: 1013.6
(M + Na) + ; measured: 1013.6 (M + Na) + .
Ac-P 33 -NH(CH 2 ) 3 -N 3 (24). P 33 = Gly-Ala-Gln-Leu-Lys-Lys-
Lys-Leu-Gln-Ala-Asn-Lys-Lys-Glu-Leu-Ala-Gln-Leu-Lys-Trp-
Lys-Leu-Gln-Ala-Leu-Lys-Lys-Lys-Leu-Ala-Gln-Gly.
The compound was prepared analogously to 1, using
3-amino-propylazide. Resin loading: 0.55 mmol g −1 (99%).
Crude yield (71%). ESI-ion trap; Mass calculated: 537.3 (M +
7H + ); 626.7 (M + 6H + ); 751.9 (M + 5H + ); 939.6 (M + 5H + );
1252.4 (M + 6H + ); measured: 537.5(6+); 626.8(5+); 752.1
(4+); 939.6; 1253.0(3+).
Ac-Gly-Gly-Ala-Asn-Pro-Asn-Ala-Ala-Gly-
NHCH 2 - (25). The compound was prepared analogously to 1,
using propargyl amine. Resin loading: 0.55 mmol g −1 (99%).
Crude yield (78%). ESI-ion trap; Mass calculated: 772.3
(M + Na) + ; measured: 772.5 (M + Na) + .
C 15 H 31 - Gly-Ala-Asn-Pro-Asn-Ala-Ala-Gly-NHCH 2 - (26).
The compound was prepared analogously to 1, usingpropargyl
amine. Resin loading: 0.55 mmol g −1 (99%). Isolated yield
(43%). Maldi-Tof; Mass calculated: 968.6 (M + Na) + ; measured:
968.5 (M + Na) + .
PS 32 -Gly-Ala-Asn-Pro-Asn-Ala-Ala-Gly-PS 20 (27). Preparation
and characterization as described in Ref. 2
18-crown-6-CH 2 C(O)-Gly-Ala-Asn-Pro-Asn-Ala-Ala-Gly-
NHCH 2 -1-aza-18-crown-6 (28). The compound was prepared
analogously to 1, using 3 equivalents of crown ether methylamine
and 3 equivalents NaCNBH 3 , followed by peptide
coupling described for 1. After deprotection of the final amino
acid BrCH 2 COOH (3 equiv.), DIPCDI (3.3 equiv.), HOBt (3.6
equiv.) and DMF were added. After shaking for 3 h the resin
was washed with DMF, 1-aza-18-crown-6 (3 equiv.) in DMF
was added and the resin was shaken for 18 h. The peptide
was cleaved with 5% H 2 OinTFAfor2h.Thefreepeptidewas
precipitated in ether, dissolved in water and lyophilized.
Resin loading 0.58 mmol g −1 (90%). Crude yield (82%).
Maldi-Tof; Mass calculated: 1250.4 (M + H) + ; measured:
1250.1 (M + H) + , 1271.1 (M + Na) + , 1287.0 (M + K) + .
Gly-Gly-Arg-Gly-Asp-Ser-Gly-NH(CH 2 ) 3 -NH-dansyl
(29). The compound was prepared analogously to 1, using
3 equivalents of N-dansyl-1,3-diaminopropane and 3 equivalents
NaCNBH 3 . Resin loading 0.45 mmol g −1 (88%). Crude
yield (64%). ESI+; Calculated mass: 894.38(M + H) + ; Measured
mass: 894.54 (M + H) + . After the first amino acid,
some product was cleaved with 5% H 2 OinTFA.ESI+; Calculated
mass 609.2147 (M + Na) + , Measured mass: 609.2122
(M + Na) + .
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Copyright © 2006 European Peptide Society and John Wiley & Sons, Ltd. J. Pept. Sci. 2006; 12: 686–692
DOI: 10.1002/psc