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Publikācija: Synthesis of Building Blocks for Carbopeptoids and Their Triazole Isoster Assembly

Publication Type Scientific article indexed in SCOPUS or WOS database
Funding for basic activity Unknown
Defending: ,
Publication language English (en)
Title in original language Synthesis of Building Blocks for Carbopeptoids and Their Triazole Isoster Assembly
Field of research 1. Natural sciences
Sub-field of research 1.4 Chemical sciences
Authors Vitālijs Rjabovs
Pāvels Ostrovskis
Daniels Posevins
Gļebs Kiseļovs
Viktors Kumpiņš
Anatolijs Mišņovs
Māris Turks
Keywords Carbohydrates / Peptidomimetics / Amino acids / Nitrogen heterocycles / Carbopeptoids
Abstract Synthetic approaches towards novel N-protected γ- and δ-furanoid sugar amino acids (SAAs) or tetrahydrofuran amino acids were developed. SAAs have emerged as valuable building blocks for the syntheses of peptide mimetics, so-called carbopeptoids. 3-C-Substituted 1,2-O-isopropylidene-α-D-allofuranose derivatives have been used as starting materials. The designed SAAs possess either cis- or trans-orientated C(3)-aminomethyl and C(4)- or C(5)-carboxylic acid functional groups attached to the 1,2-O-isopropylidene furanoid core, thus providing different spatial arrangement. Short-chain homooligomers derived from one γ-SAAs and δ-SAA were synthesized as the initial step towards exploration of novel carbopeptoids. The key intermediates of the presented SAA syntheses can be easily transformed into the molecules containing azide and terminal alkyne moieties and as such can be used for syntheses of 1,2,3-triazole isosters of peptides in the future.
DOI: 10.1002/ejoc.201500695
Hyperlink: http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201500695/abstract 
Reference Rjabovs, V., Ostrovskis, P., Posevins, D., Kiseļovs, G., Kumpiņš, V., Mišņovs, A., Turks, M. Synthesis of Building Blocks for Carbopeptoids and Their Triazole Isoster Assembly. European Journal of Organic Chemistry, 2015, Vol.2015, Iss.25, pp.5572-5584. e-ISSN 1099-0690. Available from: doi:10.1002/ejoc.201500695
Additional information Citation count:
ID 20585