Synthesis and geometry of methyl (methyl 4-O-acetyl-3-azido-2,3-dideoxy-α/β-d-arabino- and -α/β-d-ribo-hexopyranosid)uronates

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

“…Synthesised by ring-closing metathesis on 2-C-hydroxymethyl-L-erythrose acetonide (Totokotsopoulos, et al, 2008) Chain-extended Se, S, and N analogues of the glucosidase inhibitor salacinol MALDI For structure-activity studies 1-Epi-valienamine TOF (THAP) Cyclohexene -part of the structure of acarbose (Cumpstey, et al, 2008) Fluorescent fructose derivatives TOF Fluorophores 7-nitro-1,2,3-benzadiazole (NBD) and Cy5.5 for imaging breast cancer cells (Levi, et al, 2007) Fructose-fused γ-butyrolactones and lactams TOF (DHB) As GABA receptor ligands (Araújo, et al, 2008) Peracetylated C-glycoside ketones R-TOF (DHB) For EI fragmentation studies Me-3,4-di-O-Ac-1,5-anhydro-2-deoxy-D-arabino-hex-1-enopyranuronate TOF For X-ray diffraction and NMR study (Liberek, et al, 2007) Me (Me 4-O-Ac-3-azido-2,3-dideoxy-a/b-D-arabino-anda/b-D-ribo-HexpA TOF Synthesis and geometry (Tuwalska, et al, 2008a) Methyl 3-amino-2,3-dideoxyhexopyranosidic acids TOF Synthesis and conformational analysis (Tuwalska, et al, 2008b) β-D-Rhamnopyranosides TOF (DHB) 2-Naphthylmethyl ether to make a temporary linkage as a mixed acetal (Lee, et al, 2008c) S-Alkylated sulfonium ions TOF (DHB) Alkyl group on thiopentoses (Mohan, et al, 2007) Sialic acid azide TOF (DHB) Study into the mechanism of action of Trypanosoma cruzi trans-sialidase (Damager, et al, 2008) Sulfonic acid analogues of Nacetylneuraminic acid TOF First synthesis. from 1-thio-L-fucoside derivatives (Szabó, et al, 2008) Oligosaccharides α-Acarviosinyl-(1-9)-3-α -Dglucopyranosylpropen TOF From acarviosine-glucose and 3-α-Dglucopyranosylpropen Arabinofuranoside glycodynamers TOF "Dynamic" molecules by replacement of glycosidic link with oxime (Ruff & Lehn, 2007) Arabinoxylobiose TOF/TOF (DHB)…”

Synthesis and conformational analysis of methyl 3-amino-2,3-dideoxyhexopyranosiduronic acids, new sugar amino acids, and their diglycotides

“…But ascribing a concrete boat or skew-boat conformation to these coupling constants is fraught with uncertainty, especially as the NOE experiments performed for compounds 18-21 supply no significant data regarding the pyranose ring conformations. We therefore suggest that compounds with the J 4,5 7.2-8.3 Hz, and J 2a, 3 3.4-6.0 Hz coupling constants (4,7,9,14,20,25, and 26) remain in the 4 C 1 ¢ 1 C 4 conformational equilibrium, though shifted in the 4 C 1 direction ( Table 1) The findings presented in this paper show that the 4 C 1 conformation is preferably adopted by methyl 3-azido-and 3-amino-2,3-dideoxyhexopyranosiduronic acids and their derivatives with the D D-arabino and D D-lyxo configurations. Although the D D-lyxo analogs of methyl 3-amino-2,3-dideoxyhexopyranosiduronic acids were not synthesized, we can infer their conformation from the L L-lyxo enantiomers.…”

“…8,15,[21][22][23][24] The previously reported addition of hydrazoic acid to the a,b-unsaturated aldehyde derived from 3,4-di-O-acetyl-2,6-anhydro-5-deoxy-D D-lyxo-hex-5-enopyranonate (commercial name methyl 3,4-di-O-acetyl-D D-glucuronal) (1, Scheme 1) yielded methyl (methyl 4-Oacetyl-3-azido-2,3-dideoxy-a,b-D D-arabino-, and -a,b-D Dribo-hexopyranosid)uronates (2-5)-new SAA precursors. 25 This paper reports on the conversions of 2-5 into different 3-azido-and 3-amino-2,3-dideoxyhexopyranosiduronic acid derivatives. Synthesized SAAs, especially those with the D D-arabino structure, serve as potential 0008 peptide b-turn mimetics.…”

“…Methyl (methyl 4-O-acetyl-3-azido-2,3-dideoxy-a-D Darabino-(2), -b-D D-ribo-(3), -a-D D-ribo-(4), and -b-D Darabino-hexopyranosid)uronates (5)These were synthesized as previously reported 25. 3.4.…”

Oligomers and peptidomimetics consisting of methyl 3-amino-2,3-dideoxyhexopyranosiduronic acids

“…17,18 Additionally, SAAs have been introduced into the peptide backbone as non-peptide isosters to achieve desirable secondary structures. 19e24 In our previous papers the syntheses of methyl 3-amino-2,3-dideoxyhexopyranosiduronic acids with a-D-arabino, b-D-arabino, a-D-ribo, and b-D-ribo configurations, 25 and their dimers were presented. 26 The syntheses of four homo and heterooligomeric tetramers built of above mentioned methyl 3-amino-2,3-dideoxyhexopyranosiduronic acids are presented here.…”