138857-83-7Relevant academic research and scientific papers
Synthesis of glycoimmunogen Tn-Thr-PS A1 via hydrazone bond and stability optimization of PS A1 monosaccharide mimics under vaccine development conditions
Hossain,Nishat,Ghosh,Boga,Hymel,Andreana
, p. 107 - 129 (2020/02/11)
Previously, our group constructed several immunogens utilizing oxime linkage to conjugate a T-cell stimulatory zwitterionic polysaccharide PS A1 and tumor associated carbohydrate antigens (TACAs) in acetate buffer. Here, a semi-synthetic immunogen was synthesized using hydrazone conjugation between PS A1 and a glycopeptide hydrazide (α-D-GalNAc-L-Thr-NH-NH2) with an excellent loading in PBS buffer. To get robust immune response, the retention of zwitterionic character of PS A1 under vaccine construction conditions is essential. In this regard, the stability of embedded pyruvate acetal moiety in tetrasaccharide repeating unit of PS A1 can validate the retention of the dual charges. Therefore, rather than utilizing this highly immunogenic PS A1 fully, stability studies were performed with synthetic 1-thiophenyl-4,6-O-pyruvate acetal-D-galactopyranose in varying acetate buffer pHs and time intervals. Furthermore, 1-propyl-D-galactofuranose was synthesized to mimick the D-Galf of PS A1 to examine regioselective hydrazone and oxime formation with α-D-GalNAc-L-Thr-NH-NH2 and α-D-GalNAc-ONH2 moieties respectively.
Conformational Distortion Using a Molecular Lever: Synthesis and Conformational Studies of Galactoside Derivatives
H?ner, Markus,Herrstedt Hammelev, Christian,Pedersen, Christian Marcus
, p. 5532 - 5537 (2018/10/24)
Novel bicyclic d-galactose derivatives containing a molecular lever were synthesized and their conformations studied by 1H-NMR and crystallography. Increasing the bulkiness in the alkylidene ring in combination with introducing bulky O-protective groups on the pyranoside ring, causes a ring flip from a 4C1 into the axial rich 1C4 conformation. With less bulky protective groups, the pyranoside ring resides in the 4C1 conformation despite distortion of the external alkylidene ring.
Chemical synthesis of (4,6-Pyr)-Gal β1→4GlcNacβ1→3Fucβ1→OMe: A pyruvated trisaccharide related to the cell aggregation of the sponge Microciona prolifera
Deng, Shaojiang,Yu, Biao,Guo, Zhongwu,Hui, Yongzheng
, p. 439 - 452 (2007/10/03)
4,6-O-[(R)-1-carboxylethylidene] Galβ1→4GlcNAcβ1→3Fucβ1→OMe, a pyruvated trisaccharide unit involved in the aggregation factor of the marine sponge Microciona prolifera, was synthesized stereospecifically and unambiguously employing thioglycosides as glycosyl donors to construct glycosidic bonds.
Rhizobial saccharides. 2. Selective synthesis of both diastereomers of 4,6-O-pyruvylated D-glycopyranosides
Ziegler
, p. 6857 - 6860 (2007/10/02)
Both diastereomers of 4,6-O-pyruvylated glycosides S- and R-2 were selectively prepared from the corresponding 4,6-unprotected glycosides 1 by acetalation of the latter with methyl pyruvate and BF3-diethylether complex. In acetonitrile as the solvent, the thermodynamically favoured diastereomers having an axial-oriented methoxycarbonyl group are formed preferentially. In methyl pyruvate as the solvent, the diastereomers having an equatorial-oriented methoxycarbonyl group are the main products and the diastereoselectivity of the acetalation is influenced by the protecting groups at positions 2-O and 3-O of the starting glycosides 1.
Synthesis of 5-aminopentyl 4,6-O--β-D-galactopyranoside and its use as a ligand for the affinity chromatography of human serum amyloid P protein
Ziegler, Thomas,Eckhardt, Elisabeth,Strayle, Jochen,Herzog, Helmut
, p. 167 - 184 (2007/10/02)
A series of 2,3-di-O-benzoyl-D-galctopyranosides, α-allyl (5), α-benzyl (6), β-ethyl-1-thio (7), β-phenyl-1-thio (8), and α-methyl (9), were prepared from the corresponding 4,6-O-benzylidene derivatives and were acetalated in acetonitrile with methyl pyruvate, to give diastereoselectively the 2,3-di-O-benzoyl-4,6-O--D-galactopyranosides 10-16.The latter were converted into the 2,3-di-O-benzoyl-4,6-O--D-galactopyranosyl α- and β-trichloroacetimidates 19 and 20, α- and β-fluorides 21 and 22, the α-bromide 23, and the α-chloride 24, respectively.These donors, including the phenyl 1-thiogalactoside 14, reacted with 5-pentanol to give the corresponding protected β-D-galactoside 27, deblocking of which afforded the title compound 1.Binding of 1 to epoxypropyl-modified acrylamide beads gave an affinity adsorbent that was used to isolate serum amyloid P protein from human serum.
Lewis Acid-Catalysed Anomerisation and Rearrangement of Alkyl D-Glycopyranosides During Acetalisation with Methyl Pyruvate: How to Utilise it for the Preparation of 1-(Carboxyethylidene)glycopyranosyl Donors
Ziegler, Thomas,Eckhardt, Elisabeth,Herold, Gerhard
, p. 441 - 452 (2007/10/02)
The preparation of 4,6-O-(1-methoxycarbonylethylidene)-D-glycopyranosides 5 starting from 2,3-di-O-benzoyl-D-glycopyranosides 1 and their 4,6-bis-O-trimethylsilyl ethers 2 using methyl 2,2-bis(phenylthio)propionate (4) and methyl pyruvate (3), respectivel
Diastereoselective formation of pyruvylated glycosides from partly protected sugars and methyl pyruvate
Ziegler,Eckhardt,Herold
, p. 4413 - 4416 (2007/10/02)
Various partly protected sugars (gluco-, manno-, and galactopyranosides) were acetalized with methyl pyruvate in moderate to good yield with BF3-etherate as the condensing reagent. Thus, (1-methoxycarbonyl)ethylidene glycosides were obtained di
