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Original scientific paper
https://doi.org/10.5562/cca2591

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

Kristina Vlahoviček-Kahlina ; Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička c. 54, 10000 Zagreb, Croatia
Andreja Jakas ; Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička c. 54, 10000 Zagreb, Croatia

Fulltext: english, pdf (982 KB) pages 151-157 downloads: 1.057* cite
APA 6th Edition
Vlahoviček-Kahlina, K. & Jakas, A. (2015). Synthesis of Orthogonally Protected Muramic Acid Building Blocks for Solid Phase Peptide Synthesis. Croatica Chemica Acta, 88 (2), 151-157. https://doi.org/10.5562/cca2591
MLA 8th Edition
Vlahoviček-Kahlina, Kristina and Andreja Jakas. "Synthesis of Orthogonally Protected Muramic Acid Building Blocks for Solid Phase Peptide Synthesis." Croatica Chemica Acta, vol. 88, no. 2, 2015, pp. 151-157. https://doi.org/10.5562/cca2591. Accessed 18 Sep. 2021.
Chicago 17th Edition
Vlahoviček-Kahlina, Kristina and Andreja Jakas. "Synthesis of Orthogonally Protected Muramic Acid Building Blocks for Solid Phase Peptide Synthesis." Croatica Chemica Acta 88, no. 2 (2015): 151-157. https://doi.org/10.5562/cca2591
Harvard
Vlahoviček-Kahlina, K., and Jakas, A. (2015). 'Synthesis of Orthogonally Protected Muramic Acid Building Blocks for Solid Phase Peptide Synthesis', Croatica Chemica Acta, 88(2), pp. 151-157. https://doi.org/10.5562/cca2591
Vancouver
Vlahoviček-Kahlina K, Jakas A. Synthesis of Orthogonally Protected Muramic Acid Building Blocks for Solid Phase Peptide Synthesis. Croatica Chemica Acta [Internet]. 2015 [cited 2021 September 18];88(2):151-157. https://doi.org/10.5562/cca2591
IEEE
K. Vlahoviček-Kahlina and A. Jakas, "Synthesis of Orthogonally Protected Muramic Acid Building Blocks for Solid Phase Peptide Synthesis", Croatica Chemica Acta, vol.88, no. 2, pp. 151-157, 2015. [Online]. https://doi.org/10.5562/cca2591

Abstracts
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.

Keywords
dipeptide isostere; muramic acid; solid phase peptide synthesis (SPPS); sugar amino acid (SAA)

Hrčak ID: 141987

URI
https://hrcak.srce.hr/141987

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