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Synthesis of Building Blocks for Carbopeptoids and Their Triazole Isoster Assembly
Author(s) -
Rjabovs Vitālijs,
Ostrovskis Pāvels,
Posevins Daniels,
Kiseļovs Gļebs,
Kumpiņš Viktors,
Mishnev Anatoly,
Turks Māris
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500695
Subject(s) - chemistry , alkyne , amino acid , azide , stereochemistry , tetrahydrofuran , combinatorial chemistry , peptide , triazole , peptidomimetic , organic chemistry , biochemistry , catalysis , solvent
Abstract Synthetic approaches to new 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 were used as starting materials. The designed SAAs contain either cis ‐ or trans ‐oriented 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 arrangements. Short‐chain homooligomers derived from a γ‐SAA and from a δ‐SAA were synthesized as the initial step towards exploration of new carbopeptoids. The key intermediates of these SAA syntheses can easily be transformed into the corresponding molecules containing azide and terminal alkyne moieties and as such have potential for future use for the syntheses of 1,2,3‐triazole isosters of peptides.