Abstract
The preparation of a beta-galactosylated hydroxyproline derivative and its use in the multi-gram solid-phase synthesis of the potent analgesic neoglycopeptide O1.5-beta-D-galactopyranosyl [D-Met2, Hyp5]enkephalinamide is described in this paper. The most closely related impurities have been identified, isolated and characterized. Significant aspects of the synthesis and purification affecting yields and purity of both the building block and the target neoglycopeptide are discussed.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Analgesics, Opioid / chemical synthesis*
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Analgesics, Opioid / chemistry
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Analgesics, Opioid / isolation & purification*
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Enkephalin, Methionine / chemical synthesis*
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Enkephalin, Methionine / chemistry
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Enkephalin, Methionine / isolation & purification*
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Enkephalins / chemical synthesis*
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Enkephalins / chemistry
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Enkephalins / isolation & purification*
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Galactosides / chemical synthesis*
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Galactosides / chemistry
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Glycopeptides / chemical synthesis*
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Glycopeptides / chemistry
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Glycopeptides / isolation & purification*
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Glycosylation
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Hydroxyproline / analogs & derivatives*
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Hydroxyproline / chemical synthesis*
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Hydroxyproline / chemistry
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Indicators and Reagents
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Pilot Projects
Substances
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Analgesics, Opioid
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Enkephalins
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Galactosides
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Glycopeptides
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Indicators and Reagents
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O-(2,3,4,6-tetra-O-acetyl-galactopyranosyl)-N-fluoren-9-yl-methoxycarbonylhydroxyproline
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enkephalinamide, Met(2)-Hyp(5)galactopyranosyl-
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Enkephalin, Methionine
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Hydroxyproline