An unsaturated peptidomimetic assembly derived from a carbohydrate

• Published in: Journal of peptide science Vol. 10; no. 1; pp. 1 - 7
• Main Authors: Chung, Ying-Kit, Claridge, Timothy D. W., Fleet, George W. J., Johnson, Stephen W., Jones, John H., Lumbard, Keith W., Stachulski, Andrew V.
• Format: Journal Article
• Language: English
• Published: Chichester, UK John Wiley & Sons, Ltd 01.01.2004
• Subjects: Amino Sugars - chemical synthesis; Amino Sugars - chemistry; azido acids; Carbohydrate Conformation; carbohydrates; Dimerization; Galactose - analogs & derivatives; Galactose - chemistry; Hydrogen Bonding; In Vitro Techniques; Models, Molecular; Molecular Structure; unsaturated peptidomimetics
• ISSN: 1075-2617; 1099-1387
• DOI: 10.1002/psc.488

A strategy has been established for the synthesis of peptidomimetics derived from unsaturated carbohydrates, and exemplified by the use of methyl 2,6‐anhydro‐7‐azido‐3,7‐deoxy‐4,5‐O‐isopropylidene‐D‐lyxo‐hept‐2‐enonate 9 as a dipeptide ‘monomer’ which can be elaborated from either end. Selective reduction of 9 gives a protected pseudodipeptide ester suitable for use as an amino component, and saponification gives an azido acid suitable for use as a carboxyl component. The ‘dimer’ product of coupling these two components with TBTU can be similarly elaborated at either end to give a ‘trimer’, and a further cycle of selective reduction and coupling gave a ‘tetramer’, 17, a pseudo‐octapeptide. Copyright © 2003 European Peptide Society and John Wiley & Sons, Ltd.