Organic Letters
Letter
(7) Hooper, G. J.; Orjala, J.; Schatzman, R. C.; Gerwick, W. H. J. Nat.
Prod. 1998, 61, 529−533.
8) Sanchez, L. M.; Lopez, D.; Vesely, B. A.; Togna, G. D.; Gerwick,
W. H.; Kyle, D. E.; Linington, R. G. J. Med. Chem. 2010, 53, 4187−
197.
9) Iwasaki, A.; Ohno, O.; Sumimoto, S.; Ogawa, H.; Nguyen, K. A.;
Suenaga, K. Org. Lett. 2015, 17, 652−655.
10) Chatterjee, J.; Rechenmacher, F.; Kessler, H. Angew. Chem., Int.
Ed. 2013, 52, 254−269.
11) Nabika, R.; Oishi, S.; Misu, R.; Ohno, H.; Fujii, N. Bioorg. Med.
Chem. 2014, 22, 6156−6162.
12) Biron, E.; Chatterjee, J.; Ovadia, O.; Langenegger, D.; Brueggen,
(
4
(
(
(
(
J.; Hoyer, D.; Schmid, H. A.; Jelinek, R.; Gilon, C.; Hoffman, A.;
Kessler, H. Angew. Chem., Int. Ed. 2008, 47, 2595−2599.
(13) Silvi, M.; Arceo, E.; Jurberg, I. D.; Cassani, C.; Melchiorre, P. J.
Am. Chem. Soc. 2015, 137, 6120−6123.
(
14) Myers, A. G.; Yang, B. H.; Chen, H.; McKinstry, L.; Kopecky, D.
Figure 2. RP-HPLC analysis of purified 1a using an XTerra MS C-18
+
J.; Gleason, J. L. J. Am. Chem. Soc. 1997, 119, 6496−6511.
column (5 μm; 4.6 mm × 150 mm). HRMS (EI): m/z [M + Na]
+
(15) Kong, C.; Jana, N.; Driver, T. G. Org. Lett. 2013, 15, 824−827.
calculated for C H N O Na : 1093.7036, observed: 1093.7032.
60
94
8
9
(16) Thern, B.; Rudolph, J.; Jung, G. Angew. Chem., Int. Ed. 2002, 41,
2
(
307−2309.
17) Teixido,
166.
product jahanyne (1a), but should also be applicable to the
́
M.; Albericio, F.; Giralt, E. J. Pept. Res. 2005, 65, 153−
synthesis of other acetylene-containing lipopeptides which
4
−8
contain contiguous N-methylated amino acids.
Moreover,
(18) Vaisar, T.; Urban, J. J. Mass Spectrom. 1998, 33, 505−524.
(19) Echalier, C.; Al-Halifa, S.; Kreiter, A.; Enjalbal, C.; Sanchez, P.;
the methodology can be applied more generally to the synthesis
of N-methylated peptides using an SPPS-based approach.
́
Ronga, L.; Puget, K.; Verdie, P.; Amblard, M.; Martinez, J.; Subra, G.
Amino Acids 2013, 45, 1395−1403.
(
(
2
20) Hachmann, J.; Lebl, M. J. Comb. Chem. 2006, 8, 149−149.
21) Ali, A. M.; Taylor, S. D. Angew. Chem., Int. Ed. 2009, 48, 2024−
026.
ASSOCIATED CONTENT
Supporting Information
■
*
S
(22) Ali, A. M.; Taylor, S. D. J. Pept. Sci. 2010, 16, 190−199.
(23) Brieke, C.; Cryle, M. J. Org. Lett. 2014, 16, 2454−2457.
(24) Szantai-Kis, M.; Walters, C. R.; Barrett, T. M.; Hoang, E. M.;
Petersson, E. J. Synlett 2017, 28, 1789−1794.
Experimental procedures and spectral data (PDF)
(25) Siow, A.; Hung, K.-y.; Harris, P. W.; Brimble, M. A. Eur. J. Org.
Chem. 2017, 2017, 350−354.
AUTHOR INFORMATION
(26) Kavianinia, I.; Kunalingam, L.; Harris, P. W.; Cook, G. M.;
Brimble, M. A. Org. Lett. 2016, 18, 3878−3881.
■
*
(27) Rodríguez, H.; Suarez, M.; Albericio, F. J. Pept. Sci. 2010, 16,
ORCID
1
36−140.
(28) Schnitzer, T.; Wennemers, H. J. Am. Chem. Soc. 2017, 139,
5356−15362.
1
(
Notes
29) Falb, E.; Yechezkel, T.; Salitra, Y.; Gilon, C. J. Pept. Res. 1999,
5
3, 507−517.
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
We acknowledge financial support from the Maurice Wilkins
Centre for Molecular Biodiscovery and The University of
Auckland for the award of a Doctoral Scholarship to G.O. The
̈
authors would also like to thank Chloe Marcourt (The
University of Auckland) for the synthesis of Oep.
REFERENCES
■
(
1) Costa, M.; Garcia, M.; Costa-Rodrigues, J.; Costa, M. S.; Ribeiro,
M. J.; Fernandes, M. H.; Barros, P.; Barreiro, A.; Vasconcelos, V.;
Martins, R. Mar. Drugs 2014, 12, 98−114.
(
2) Mooberry, S. L.; Leal, R. M.; Tinley, T. L.; Luesch, H.; Moore, R.
E.; Corbett, T. H. Int. J. Cancer 2003, 104, 512−521.
(
(
3) Polakis, P. Pharmacol. Rev. 2016, 68, 3−19.
4) Chen, H.; Feng, Y.; Xu, Z.; Ye, T. Tetrahedron 2005, 61, 11132−
1
1140.
(
5) Okamoto, S.; Iwasaki, A.; Ohno, O.; Suenaga, K. J. Nat. Prod.
015, 78, 2719−2725.
6) Simmons, T. L.; Engene, N.; Uren
Barría, E.; Gerwick, L.; Gerwick, W. H. J. Nat. Prod. 2008, 71, 1544−
550.
2
(
̃
a, L. D.; Romero, L. I.; Ortega-
1
D
Org. Lett. XXXX, XXX, XXX−XXX