Carbon-branched delta-tetrahydrofuran sugar amino acids (SAAs) as dipeptide isostere scaffolds

Carbon-branched delta-tetrahydrofuran sugar amino acids (SAAs) as dipeptide isostere scaffolds

The synthesis of the first branched sugar amino acid (SAA) scaffolds [methyl (3R,4R,5R)-5-azidomethyl-3,4-dihydroxy-tetrahydrofuran-3-carboxylate and methyl (3R,4R,5S)-5-azidomethyl-3,4-dihydroxy-tetrahydrofuran-3-carboxylate] by an efficient intramolecular displacement of a highly hindered neopenty...

Descrición completa

Detalles Bibliográficos
Main Authors:	Simone, M, Edwards, A, Tranter, G, Fleet, G
Formato:	Journal article
Idioma:	English
Publicado:	2008

Títulos similares

Designing secondary structures: 5-azidomethyl tetrahydrofuran-2-carboxylates as carbohydrate-derived dipeptide isosteres
por: Smith, MD, et al.
Publicado: (1999)

Designing secondary structures: 5-azidomethyl tetrahydrofuran-2-carboxylates as carbohydrate-derived dipeptide isosteres.
por: Smith, M, et al.
Publicado: (1999)

Designing secondary structures: 5-azidomethyl tetrahydrofuran-2-carboxylates as carbohydrate-derived dipeptide isosteres
por: Smith, M, et al.
Publicado: (1999)

Branched tetrahydrofuran alpha,alpha-disubstituted-delta-sugar amino acid scaffolds from branched sugar lactones: a new family of foldamers?
por: Simone, M, et al.
Publicado: (2005)

A compendium of sugar amino acids (SAA): scaffolds, peptide- and glyco-mimetics
por: Risseeuw, M, et al.
Publicado: (2007)

Conformational studies of oligomeric oxetane-based dipeptide isosteres derived from L-rhamnose or D-xylose.
por: Johnson, S, et al.
Publicado: (2005)

Pseudoenantiomeric oxetane delta-amino acid scaffolds derived from L-rhamnose and D-xylose: D/L-alanine-D-serine and glycine-L-serine dipeptide isosteres
por: Johnson, S, et al.
Publicado: (2004)

Tetrahydrofuran-based amino acids as library scaffolds.
por: Edwards, A, et al.
Publicado: (2004)

Cyclic oligomers of oxetane-based dipeptide isosteres derived from L-rhamnose.
por: Fleet, G, et al.
Publicado: (2006)

Cyclic oligomers of oxetane-based dipeptide isosteres derived from L-rhamnose
por: Fleet, G, et al.
Publicado: (2006)

C-3 branched δ-3,5-cis- and trans-THF sugar amino acids: synthesis of the first generation of branched homooligomers.
por: Simone, M, et al.
Publicado: (2011)

Templated scaffolds of cis- and trans-tetrahydrofuran gamma-amino acids: gamma-azido-beta-hydroxy-tetrahydrofuran-2-carboxylates from pentono-delta-lactones
por: Sanjayan, G, et al.
Publicado: (2003)

The synthesis of oligomers of oxetane-based dipeptide isosteres derived from L-rhamnose or D-xylose.
por: Johnson, S, et al.
Publicado: (2005)

Classification of conformation for sugar amino acid systems using chiroptical spectroscopy.
por: Edwards, A, et al.
Publicado: (2006)

Chiroptical spectroscopy and sugar amino acid systems
por: Edwards, A, et al.
Publicado: (2005)

Recent progress in the racemic and enantioselective synthesis of monofluoroalkene-based dipeptide isosteres
por: Myriam Drouin, et al.
Publicado: (2017-12-01)

Bend ribbon-forming tetrahydrofuran amino acids.
por: Smith, M, et al.
Publicado: (2003)

Spectroscopic studies of oligomers containing 2,5-trans furanoid sugar amino acids.
por: Edwards, A, et al.
Publicado: (2008)

CYCLIC SULFATES OF DELTA-LACTONES IN THE SYNTHESIS OF TETRAHYDROFURANS TETRAHYDROPYRANS AND CYCLOHEXANES
por: Skead, B, et al.
Publicado: (1993)

Synthesis of oligomers of tetrahydrofuran amino acids: furanose carbopeptoids
por: Smith, M, et al.
Publicado: (1998)

Synthesis of tetrahydrofuran templated beta- and gamma-amino acid carbopeptoids.
por: Watterson, M, et al.
Publicado: (2000)

A novel series of oligomers from 4-aminomethyl-tetrahydrofuran-2-carboxylates with 2,4-cis and 2,4-trans stereochemistry
por: Edwards, A, et al.
Publicado: (2006)

Synthesis of 4-aminomethyl-tetrahydrofuran-2-carboxylates with 2,4-cis and 2,4-trans relationships
por: Edwards, A, et al.
Publicado: (2006)

Tetrahydrofuran amino acids: Secondary structure in tetrameric and octameric carbopeptoids derived from a D-allo 5-(aminomethyl)tetrahydrofuran-2-carboxylic acid
por: Hungerford, N, et al.
Publicado: (2000)

3-Azido-tetrahydrofuran carboxylates as scaffolds for oligomers of beta-amino-THF carboxylic acids
por: Marsh, P
Publicado: (2002)

Amino sugars and their glycosides
por: Hindle, N, et al.
Publicado: (1995)

Tetrahydrofuran amino acids - versatile building blocks for unnatural biopolymers: lack of secondary structure in oligomeric carbopeptoids derived from a D-galacto-5-(aminomethyl) tetrahydrofuran-2-carboxylic acid
por: Brittain, D, et al.
Publicado: (2000)

Complex tetrahydrofurans from carbohydrate lactones: THF amino acids as building blocks for unnatural biopolymers
por: Long, D, et al.
Publicado: (2002)

Tetrahydrofuran amino acids: beta- and gamma-azidotetrahydrofurancarboxylic acid monomers derived from D-glucoheptonolactone as building blocks for beta- and gamma-oligopeptides
por: Hungerford, N, et al.
Publicado: (2000)

Tetrahydrofuran alpha-azido esters: Precursors of anomeric alpha-amino acid monomers via radical bromination
por: Smith, M, et al.
Publicado: (1999)

ACID-CATALYZED TRANSFORMATION OF ALPHA-TRIFLUOROMETHANESULFONATES OF GAMMA-LACTONES AND DELTA-LACTONES INTO 2,5-DISUBSTITUTED HOMOCHIRAL TETRAHYDROFURANS
por: Wheatley, J, et al.
Publicado: (1993)

Selective Photocyclization of Amino Acids in Dipeptides
por: Stephan Sauer, et al.
Publicado: (1997-01-01)

Amino-sugar glycosidase inhibitors: versatile tools for glycobiologists.
por: Winchester, B, et al.
Publicado: (1992)

Pentafluorophenyl (3R,4R,5R)-5-{[(3R,4R,5R)-5-azidomethyl-3,4-dimethoxy-2,3,4,5-tetrahydro-furan-3-carbonylamino]methyl}-3,4-dimethoxy-2,3,4,5-tetrahydrofuran-3-carboxylate
por: Punzo, F, et al.
Publicado: (2006)

A compendium of cyclic sugar amino acids and their carbocyclic and heterocyclic nitrogen analogues.
por: Risseeuw, M, et al.
Publicado: (2013)

Plagiarizing plants: amino sugars as a class of glycosidase inhibitors.
por: Fleet, G, et al.
Publicado: (1990)

PLAGIARIZING PLANTS - AMINO-SUGARS AS A CLASS OF GLYCOSIDASE INHIBITORS
por: Fleet, G, et al.
Publicado: (1990)

PLAGIARIZING PLANTS - AMINO-SUGARS AS A CLASS OF GLYCOSIDASE INHIBITORS
por: Fleet, G, et al.
Publicado: (1990)

Sugar amino acids at the anomeric position of carbohydrates: synthesis of spirocyclic amino acids of 6-deoxy-L-lyxofuranose
por: Bleriot, Y, et al.
Publicado: (2006)

Change in specificity of glycosidase inhibition by N-alkylation of amino sugars.
por: al Daher, S, et al.
Publicado: (1989)