2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-b-D-glucopyranosyl-Fmoc-asparagine
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2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-b-D-glucopyranosyl-Fmoc-asparagine

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2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-b-D-glucopyranosyl-Fmoc-asparagine is an essential compound within the realm of biomedicine, assuming a paramount role in the research of targeting diverse pathologies, notably cancer and autoimmune conditions. Pivotal in targeted drug delivery strategies, this product showcases its propensity for amplified efficacy and diminished adversities. Its distinct configuration and characteristics facilitate the specific targeting of afflicted cells and the administration of therapeutic advantages.

Category
Fmoc-Amino Acids
Catalog number
BAT-008001
CAS number
131287-39-3
Molecular Formula
C33H37N3O13
Molecular Weight
683.66
2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-b-D-glucopyranosyl-Fmoc-asparagine
IUPAC Name
(2S)-4-[[(2R,3R,4R,5S,6R)-3-acetamido-4,5-diacetyloxy-6-(acetyloxymethyl)oxan-2-yl]amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxobutanoic acid
Synonyms
N-Fmoc-N-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-L-asparagine; GlcNAc L-asparagine; Fmoc-L-Asn(GlcNAc(Ac)3-beta)-OH; Fmoc-L-Asn(GlcNAc4)-OH; 2N-Fmoc-4N-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-b-D-glucopyranosyl)-L-asparagine; N2-​[(9H-​fluoren-​9-​ylmethoxy)​carbonyl]​-​N-​[3,​4,​6-​tri-​O-​acetyl-​2-​(acetylamino)​-​2-​deoxy-​β-​D-​glucopyranosyl]​-L-​Asparagine
Appearance
White to off white powder
Purity
≥95% by HPLC
Density
1.4±0.1 g/cm3
Boiling Point
934.7±65.0°C at 760 mmHg
Storage
Store at RT
InChI
InChI=1S/C33H37N3O13/c1-16(37)34-28-30(48-19(4)40)29(47-18(3)39)26(15-45-17(2)38)49-31(28)36-27(41)13-25(32(42)43)35-33(44)46-14-24-22-11-7-5-9-20(22)21-10-6-8-12-23(21)24/h5-12,24-26,28-31H,13-15H2,1-4H3,(H,34,37)(H,35,44)(H,36,41)(H,42,43)/t25-,26+,28+,29+,30+,31+/m0/s1
InChI Key
QOACISSHGAAMLK-MJCYOTSPSA-N
Canonical SMILES
CC(=O)NC1C(C(C(OC1NC(=O)CC(C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24)COC(=O)C)OC(=O)C)OC(=O)C

2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-Fmoc-asparagine is a complex compound with multiple applications in biochemical research and pharmaceutical development. Here are some key applications of 2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-Fmoc-asparagine:

Glycosylation Studies: 2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-Fmoc-asparagine is used in the study of protein glycosylation. It allows researchers to mimic natural glycan structures and study their biological roles. This is crucial for understanding cell-cell communication, immune responses, and disease mechanisms involving glycoproteins.

Peptide Synthesis: This compound is integral in the synthesis of glycopeptides. It provides a glycosylated building block that can be incorporated into peptide chains. This capability is valuable for creating peptides with specific glycan structures, which are often important for studying protein folding, stability, and interactions.

Drug Development: 2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-Fmoc-asparagine can be used in the development of novel pharmaceuticals. By including this glycosylated amino acid in drug molecules, researchers can improve drug solubility, stability, and bioavailability. This approach is particularly relevant in the design of peptide-based therapeutics and vaccines.

Bioconjugation: In bioconjugation techniques, this compound aids in the attachment of glycan motifs to proteins and other biomolecules. This can be used to label or modify proteins for various bioanalytical applications. For example, tagging enzymes with glycan structures can assist in tracking their cellular localization and interactions.

1. Practical synthesis of the 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucosides of Fmoc-serine and Fmoc-threonine and their benzyl esters
Ivone Carvalho, Shona L Scheuerl, K P Ravindranathan Kartha, Robert A Field Carbohydr Res. 2003 May 1;338(10):1039-43. doi: 10.1016/s0008-6215(03)00071-5.
Mercuric bromide-promoted glycosylation of Fmoc-Ser-OBn and Fmoc-Thr-OBn with 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-alpha-D-glucopyranosyl chloride in refluxing 1,2-dichloroethane gave the corresponding beta-glycosides in good yields (64 and 62%, respectively). Direct coupling of the commercially available Fmoc-Ser-OH and Fmoc-Thr-OH carboxylic acids under similar conditions gave the corresponding beta-glycosides, possessing free carboxyl groups, in moderate yields (50 and 40%, respectively).
2. N-(2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-alpha-D-galactopyranosyloxy)succinimide
O Renaudet, P Dumy, C Philouze, M T Averbuch-Pouchot Acta Crystallogr C. 2001 May;57(Pt 5):649-50. doi: 10.1107/s0108270101003377. Epub 2001 May 15.
The crystal structure of the title compound, C18H24N2O11, a GalNAc mimic containing an alpha-glycosyloxysuccinimide linkage, has been determined. The pyranose ring geometry is an almost perfect (4)C(1) chair. The torsion angle of the exocyclic hydroxymethyl group is shown to be gauche-trans with respect to O1 and C4, respectively.
3. The synthesis of 2-acetamido-2-deoxy-6-O-beta-D-mannopyranosyl-D-glucose
M A Shaban, I E Ary, D A Jeanloz, R W Jeanloz Carbohydr Res. 1975 Dec;45:105-14. doi: 10.1016/s0008-6215(00)85870-x.
4,6-Di-O-acetyl-2,3-O-carbonyl-alpha-D-mannopyranosyl bromide was condensed with benzyl 2-acetamido-3,4-di-O-acetyl-2-deoxy-alpha-D-glucopyranoside in the presence of silver carbonate to give crystalline benzyl 2-acetamido-3,4-di-O-acetyl-2-deoxy-6-O-(4,6-di-O-acetyl-2,3-O-carbonyl-beta-D-mannopyranosyl)-alpha-D-glucopyranoside in 32% yield. Removal of the protective O-acetyl and cyclic carbonate groups gave the crystalline benzyl alpha-glycoside of the disaccharide, which was catalytically hydrogenolyzed to yield the crystalline, title compound. Proof of the anomeric configuration of the interglycosidic linkage was obtained by comparison of the physical, spectral, and chromatographic properties of the disaccharide and its derivatives with those of the previously prepared alpha-D-linked analog.
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