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- W2121620828 abstract "Work within the Polt laboratory has focussed on the exploration and exploitation of carbohydrate moieties in the design and synthesis of opiate glycopeptides. These glycopeptides have been synthesized based on the pharmacophore D-Cys -enkephalin (DCDCE) [1]. A -D-glucose-containing analog of DCDCE, LSZ-1025, displayed potent analgesia when administered peripherally [2,3]. In an effort to understand the role of the amino acid glycoside in both penetration of the blood-brain barrier (BBB) and opiate receptor binding and stimulation, a series of glycopeptides were synthesized. This work reflects the optimized synthesis of several enkephalin glycopeptides, represented by several structural modifications. Incorporation of D-amino acid glucosides to test the environment of the amino acid-glycoside linkage, variance of the glycan moiety on serine to verify the impact of different sugars, and implementation of several different pharmacophores, such as in SAM-1095 where a linear pharmacophore [4] was used, highlight our design rationale. The impact of these changes was assessed after detailed pharmacological testing." @default.
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- W2121620828 date "2006-05-16" @default.
- W2121620828 modified "2023-10-14" @default.
- W2121620828 title "Synthesis of several O-glycopeptide analogs of enkephalin" @default.
- W2121620828 cites W2007074158 @default.
- W2121620828 cites W2016275972 @default.
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- W2121620828 doi "https://doi.org/10.1007/0-306-46881-6_8" @default.
- W2121620828 hasPublicationYear "2006" @default.
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