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- W34706147 abstract "The spatial requirements for protein chemistry and biology may be explored through the employment of azabicyclo[X.Y.0]alkane amino acids as rigid dipeptide analogs that restrain the backbone and side-chain conformations of the native peptide [1]. We introduced a practical and versatile means to access enantiopure alkyl-branched azabicycloalkane amino acids via a Claisen condensation/alkylation/reductive amination/lactam cyclization sequence [2]. This route provided 5and 7-benzyl as well as 5,7-dibenzyl indolizidinone amino acids 1–3 (Fig. 1), which can serve in constrained mimics of peptides that possess phenylalanine moieties. For example, 7-benzyl indolizidinone amino acid 2 was incorporated into analogs of Leu-enkephalin using solution-phase peptide synthesis [3]. Striving to extend our methodology to synthesize azabicycloalkane amino acids possessing heteroatomic side-chain groups, we have now synthesized 5and 7-hydroxymethyl indolizidinone amino esters 4 and 5. The hydroxymethyl group may mimic the side-chain of serine and offers the potential for glycosylation and phosphorylation of the rigid dipeptide. Furthermore, the hydroxymethyl group can serve as an entrance towards the preparation of a variety of rigid dipeptides having different side-chains, as demonstrated by the synthesis of constrained Glu-Pro surrogate 6 via oxidation of 4." @default.
- W34706147 created "2016-06-24" @default.
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- W34706147 date "2006-05-16" @default.
- W34706147 modified "2023-10-01" @default.
- W34706147 title "Mimicry of peptide backbone and side-chain functions: Syntheses of 5- and 7-hydroxymethyl indolizidinone amino acids and indolizidinone amino dicarboxylate, constrained Ser-Pro and Glu-Pro surrogates" @default.
- W34706147 cites W2083011529 @default.
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- W34706147 doi "https://doi.org/10.1007/0-306-46881-6_62" @default.
- W34706147 hasPublicationYear "2006" @default.
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