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

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)…”

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

“…These findings agree well with our earlier investigations, which have identified that the 4 C 1 conformation of monomeric 3-amino-2,3-dideoxy-D-ribo-hexopyranosiduronic acids and their derivatives is less stable than the 4 C 1 form of their D-arabino analogs. 26 As a consequence, the families of compound 13 differ noticeably with the j 1 , j 2 and j 3 dihedral angle values (Fig. 6) and the hydrogen bond network (Table 2), which demonstrates the high flexibility of this tetramer in solution.…”

“…Such results are fully in agreement with our previous conclusions based solely on 1 H NMR spectra. 26 The dimers studied using MD differ from each other with a hydrogen bond network. Thus, the structures of the (a-D-arabino) 2 (1) are not stabilized by any hydrogen bonding, whereas the (b-D-arabino) 2 (2) ones are stabilized by the OH 2 eCO 1 hydrogen bond (Table 1).…”

“…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. In search of the rigid and bent secondary structures consisting of SAAs, studies on these tetramers and dimers conformations are performed on the basis of molecular dynamics (MD), supplemented by NMR data, and CD spectroscopy.…”

AApeptides as a New Class of Peptidomimetics to Regulate Protein-Protein Interactions

“…Compared to traditional peptides, peptidomimetics have great proteolytic and metabolic stability and are believed to be less immunogenic, also with an enhanced bioavailability (Patch et al 2002;Goodman et al 2007;Wu et al 2008). The development of peptidomimetics to disrupt MDM2/p53 has led to a diverse set of oligomers such as -peptides (Seebach et al 1996;Cheng et al 2001;Kritzer et al 2005), -and -peptides (Arndt et al 2004;Trabocchi et al 2005;Kumbhani et al 2006), / -peptides (Horne et al 2008;Horne et al 2009), azapeptides (Graybill et al 1992;Lee et al 2002), -aminoxy-peptides (Li et al 2008), sugar-based peptides (Risseeuw et al 2007;Tuwalska et al 2008), peptoids (Simon et al 1992), oligoureas (Boeijen et al 2001;Violette et al 2005), polyamides (Dervan 1986), and phenylene ethynylenes (Nelson et al 1997), etc. Nonetheless, the development of peptidomimetics is far less straightforward, with the major limit lying in the availability of framework (Goodman et al 2007).…”