Stereocontrolled transformation of nitrohexofuranoses into cyclopentylamines via 2-oxabicyclo[2.2.1]heptanes. Part 2: Synthesis of (1S,2R,3S,4S,5R)-3,4,5-trihydroxy-2-aminocyclopentanecarboxylic acid

Soengas, Raquel G.; Pampı́n, M. Begoña; Estévez, Juan C.; Estévez, Ramón J.

doi:10.1016/j.tetasy.2004.11.034

Cited by 25 publications

(8 citation statements)

References 15 publications

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“…3,4,5-Trihydroxy-2-aminocyclopentanecarboxylic acid enantiomers 28 and 29 were prepared through a strategically new protocol: from D-glucose or from L-iodose. 17 The strategy is based on the transformations of nitrofuranose to cyclopentylamine derivatives via an intramolecular cyclization to a 2-oxabicyclo[2.2.1]heptane derivative, followed by selective ring opening.…”

Section: Cyclic Amino Acids From Natural Sourcesmentioning

confidence: 99%

Application of alicyclic β-amino acids in peptide chemistry

2006

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The self-organizing beta-peptides have attracted considerable interest in the fields of foldamer chemistry and biochemistry. These compounds exhibit various stable secondary structure motifs that can be exploited to construct biologically active substances and nanostructured tertiary structures. The secondary structures can be controlled via the beta-amino acid sequence, and cyclic beta-amino acid residues play a crucial role in the design. The most important procedures for the preparation of cyclic beta-amino acid monomers and peptides are discussed in this tutorial review. Besides the secondary structure design principles, the methods of folded structure detection are surveyed.

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Section: Cyclic Amino Acids From Natural Sourcesmentioning

confidence: 99%

Application of alicyclic β-amino acids in peptide chemistry

2006

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“…35 Application of this approach to L-idose nitrosugar derivative 4 provided the first polyhydroxylated cis-2-aminocyclopentanecarboxylic acid 6 (Scheme 1). 36 Nevertheless, this strategy turned out unsuitable for preparing peptides based on these β-amino acids, due to the low global yields achieved for 3a (12% yield, 7 steps), 3b (8% yield, 9 steps) and 6 (15% yield, 7 steps). Furthermore, the scope of this synthetic strategy is relatively limited, because it can provide direct access to only eight polyhydroxylated cyclopentane β-amino acids, i.e.…”

Section: Introductionmentioning

confidence: 99%

Polyhydroxylated cyclopentane β-amino acids derived from D-mannose and D-galactose: synthesis and protocol for incorporation into peptides

Fernández

Balo

et al. 2021

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A stereoselective synthesis of polyhydroxylated cyclopentane β-amino acids from hexoses is reported.The reaction sequence comprises as key steps a Ring Closing Metathesis of a polysubstituted diene intermediate, followed by the stereoselective aza-Michael functionalization of the resulting cyclopent-1ene-1-carboxylic acid ester. Examples of synthesis of polysubstituted 2-aminocyclopentanecarboxylic acid derivatives starting from protected D-mannose and D-glucose are presented. A general protocol for the incorporation of these highly functionalized alicyclic β-amino acids into peptides is also reported.

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“…33 Application of this approach to L-idose nitrosugar derivative 4 provided the first polyhydroxylated cis-2-aminocyclopentanecarboxylic acid 6 (Scheme 1). 34 Nevertheless, this strategy turned out unsuitable for preparing peptides based on these β-amino acids, due to the low global yields achieved for 3a (12% yield, 7 steps), 3b (8% yield, 9 steps) and 6 (15% yield, 7 steps). Furthermore, the scope of this synthetic strategy is relatively limited, because it can provide direct access to only eight polyhydroxylated cyclopentane β-amino acids, i.e.…”

Section: Introductionmentioning

confidence: 99%