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Synthesis of Orthogonally Protected Muramic Acid Building Blocks for Solid Phase Peptide Synthesis

Vlahoviček-Kahlina, Kristina; Jakas, Andreja (2015) Synthesis of Orthogonally Protected Muramic Acid Building Blocks for Solid Phase Peptide Synthesis. Croatica Chemica Acta, 88 (2). pp. 151-157. ISSN 0011-1643

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Muramic acid is found in many peptide natural products containing oligo(poly)saccharide moieties. Taking into consideration that the Fmoc methodology is routinely used for solid-phase peptide synthesis, preparation of orthogonally protected muramic acid building blocks for total solid-phase synthesis of these natural products is of particular practical importance. Herein a simple and efficient synthesis of benzyl 2-amino-4, 6-O-benzylidene-3-O-[(R)-1-carboxyethyl]-2-deoxy-N-9-fluorenylmethyloxycarbonyl-α- D -glucopyranoside (6) from N-acetylglucosamine (1) is described. Important improvements over previous synthetic approaches to glucopyranosides 2 (benzyl 2-acetamido-2-deoxy-α- D -glucopyranoside) and 3 (benzyl 2-acetamido-4, 6-O-benzylidene-2-deoxy-α- D -glucopyranoside), key building blocks in preparation of 6, include synthesis simplification and efficient isolation and purification. Optically pure (S)-2-chloropropionic acid 7 was prepared and introduced to the positon 3-O of sugar moiety to give compound 4 (benzyl 2-acetamido-4, 6-O-benzylidene-3-O-[(R)-1-carboxyethyl]-2-deoxy-α- D -glucopyranoside) with the (R)-configuration of the lactyl side-chain in excellent overall yield and optical purity. Deacetylation of amino group gave compound 5 (benzyl 2-amino-4, 6-O-benzylidene-3-O-[(R)-1-carboxyethyl]-2-deoxy-α-D-glucopyranoside) suitable for incorporation of the Fmoc protecting group to give protected muramic acid derivative 6, a useful building block in peptide synthesis.

Item Type: Article
Uncontrolled Keywords: dipeptide isostere; muramic acid; solid phase peptide synthesis (SPPS); sugar amino acid (SAA)
Subjects: NATURAL SCIENCES > Chemistry
Divisions: Division of Organic Chemistry and Biochemistry
Project titleProject leaderProject codeProject type
Chemical transformations of natural compounds (Kemijske preobrazbe prirodnih spojeva)Lidija Varga-Defterdarović098-0982933-2936MZOS
Depositing User: Andreja Jakas
Date Deposited: 02 May 2016 09:22
DOI: 10.5562/cca2591

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