Synthesis of Nanotubule-Forming Cyclic Octapeptides via an Fmoc Strategy
Keyword(s):
New syndiotactic cyclic octapeptides, namely cyclo(–D-Phe-L-Asp–D-Phe–L-Asn–D-Phe–L-Asp–D-Phe–L-Asn–) (1) and cyclo(–D-N-MeAla–L-Asp–D-N-MeAla–L-Asn–D-N-MeAla–L-Asp–D-N-MeAla–L-Asn–) (2), have been prepared, and preliminary structural studies have been conducted. The synthesis of the linear peptides was performed by using Fmoc chemistry, and head-to-tail cyclization was accomplished by using an orthogonal protection strategy and a support-bound cyclization step. Acidification of aqueous solutions of cyclic octapeptide (1) initiated formation of needlelike crystals whose morphology and infrared absorption behaviour suggested that they were hydrogen-bonded nanotubular aggregates of (1).
1960 ◽
Vol 82
(19)
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pp. 5156-5160
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1992 ◽
Vol 30
(12)
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pp. 1241-1246
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Hydrogen-Bonded Cluster Formation and Hydrophobic Solute Association in Aqueous Solutions of Ethanol
1995 ◽
Vol 99
(1)
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pp. 462-468
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1989 ◽
Vol 93
(11)
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pp. 4674-4677
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Keyword(s):
Simultaneous infrared absorption in a mixture of CO2 and H2O: The role of hydrogen-bonded aggregates
1994 ◽
Vol 52
(3-4)
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pp. 295-301
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1993 ◽
Vol 5
(1)
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pp. 109-117
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