Abstract
A new component for the solid phase peptide synthesis of lipopeptide, 2-[(4R,5R)-5-({[(9H-fluoren-9-yl)methoxy]carbonylaminomethyl}-2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]acetic acid (2), was designed and synthesized from (-)-2,3-O-isopropylidene-D-threitol (3) in 4 steps. The key step was the selective alkylation of 3 with benzyl bromoacetate in the presence of Cs2CO3. Vasoactive intestinal peptide (VIP)-lipopeptide (1) incorporating this linker was synthesized by solid phase peptide synthesis.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Acetates / chemistry
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Alkylation
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Carbonates / chemistry
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Cesium / chemistry
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Dioxolanes / chemical synthesis*
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Dioxolanes / chemistry
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Drug Carriers / chemistry*
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Liposomes / chemistry*
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Solid-Phase Synthesis Techniques
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Vasoactive Intestinal Peptide / chemical synthesis*
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Vasoactive Intestinal Peptide / chemistry
Substances
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Acetates
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Carbonates
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Dioxolanes
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Drug Carriers
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Liposomes
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Cesium
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Vasoactive Intestinal Peptide
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bromoacetate
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cesium carbonate