Nonphosphorylated Pentapeptide Motif
Journal of Medicinal Chemistry, 2006, Vol. 49, No. 5 1595
H)+, found 978.3. tR ) 15.1 min (10-70% of solvent B in 30 min,
purity 98%); tR ) 21.6 min (10-70% of solvent C in 30 min, purity
97%).
Cyclo-(CH2-CO-Adi-Leu-(3′-CO2H-Tyr)- Ac6c-Asn-Ava-Cys
(O))-amide (S) (peptide 9c). ESI-MS, m/z: calc. 978.1 (M + H)+,
found 978.1. tR ) 15.1 min (10-70% of solvent B in 30 min, purity
98%); tR ) 22.6 min (10-70% of solvent C in 30 min, purity 99%).
Cyclo-(CH2-CO-Gla-Leu-(3′-NH2-Tyr)-Ac6c-Asn-Ava-Cys)-
amide (peptide 10a). ESI-MS, m/z: calc. 1001.2 (M + K)+, found
1001.3. tR ) 16.2 min (10-70% of solvent B in 30 min, purity
98%); tR ) 24.3 min (10-70% of solvent C in 30 min, purity 97%).
Cyclo-(CH2-CO-Gla-Leu-(3′-NH2-Tyr)-Ac6c-Asn-Ava-Cys (O))-
amide (R) (peptide 10b). ESI-MS, m/z: calc. 977.1 (M - H)-,
found 977.1. tR ) 15.7 min (10-70% of solvent B in 30 min, purity
99%). tR ) 23.8 min (10-70% of solvent C in 30 min, purity 97%).
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Cyclo-(CH2-CO-Gla-Leu-(3′-NH2-Tyr)-Ac6c-Asn-Ava-Cys (O))-
amide (S) (peptide 10c). ESI-MS, m/z: calc. 977.1 (M - H)-,
found 977.3. tR ) 15.9 min (10-70% of solvent B in 30 min, purity
96%); tR ) 23.8 min (10-70% of solvent C in 30 min, purity 95%).
Cyclo-(CH2-CO-Gla-Leu-(3′-NH2-Tyr)-Ac6c-Asn-â-Ala-Cys)-
amide (peptide 11a). ESI-MS, m/z: calc. 919.0 (M - H)-, found
918.4. tR ) 15.7 min (10-70% of solvent B in 30 min, purity 99%);
tR ) 22.4 min (10-70% of solvent C in 30 min, purity 99%).
Cyclo-(CH2-CO-Gla-Leu-(3′-NH2-Tyr)-Ac6c-Asn-â-Ala-Cys-
(O))-amide (R) (peptide 11b). ESI-MS, m/z: calc. 935.0 (M -
H)-, found 934.3. tR ) 15.7 min (10-70% of solvent B in 30 min,
purity 98%); tR ) 23.7 min (10-70% of solvent C in 30 min, purity
96%).
Cyclo-(CH2-CO-Gla-Leu-(3′-NH2-Tyr)-Ac6c-Asn-â-Ala-
Cys (O))-amide (S) (peptide 11c). ESI-MS, m/z: calc. 935.0 (M
- H)-, found 934.3. tR ) 15.7 min (10-70% of solvent B in 30
min, purity 98%); tR ) 24.3 min (10-70% of solvent C in 30 min,
purity 99%).
Cyclo-(CH2-CO-Gla-Leu-(3′-NH2-Tyr)- Ac6c-Asn -Cys)-
amide (peptide 12a). ESI-MS, m/z: calc. 963.0 (M - H)-, found
962.3. tR ) 15.6 min (10-70% of solvent B in 30 min, purity 99%);
tR ) 22.4 min (10-70% of solvent C in 30 min, purity 98%).
Cyclo-(CH2-CO-Gla-Leu-(3′-NH2-Tyr)-Ac6c-Asn-Cys (O))-
amide (R) (peptide 12b). ESI-MS, m/z: calc. 878.8 (M+), found
878.3. tR ) 14.9 min (10-70% of solvent B in 30 min, purity 99%);
tR ) 23.5 min (10-70% of solvent C in 30 min, purity 95%).
Cyclo-(CH2-CO-Gla-Leu-(3′-NH2-Tyr)-Ac6c-Asn-Cys (O))-
amide (S) (peptide 12c). ESI-MS, m/z: calc. 878.8 (M+), found
878.3. tR ) 15.1 min (10-70% of solvent B in 30 min, purity 99%);
tR ) 24.2 min (10-70% of solvent C in 30 min, purity 97%).
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Acknowledgment. Appreciation is expressed to Prof. Xu
Shen and his colleagues of the DDDC at SIMM for their kind
assistance with the Biacore 3000 instrument. The authors are
also thankful for Dr. Marc C. Nicklaus of LMC at NCI for his
helpful advise with the molecular modeling. This work was
financially supported in part by Chinese Academy of Sciences
(No. KSCX1-S.W.-11) and Ministry of Science and Technology
of China (No. 2004CB518903), and in part by the intramural
research program of the National Cancer Institute, National
Institutes of Health (No. NO1-CO-12400).
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