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

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2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-b-D-glucopyranosyl-Fmoc serine, an indispensable constituent in the realm of biomedicine, exhibits a profound impact on pharmaceutical progress, specifically in combating diverse afflictions. Its prominence extends to the creation of unprecedented antiviral and anticancer modalities, facilitation of precision drug transportation mechanisms, and exploration of intricate cellular communication routes.

Category
Fmoc-Amino Acids
Catalog number
BAT-015306
CAS number
160067-63-0
Molecular Formula
C32H36N2O13
Molecular Weight
656.63
2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-b-D-glucopyranosyl-Fmoc serine
Size Price Stock Quantity
100 mg $439 In stock
IUPAC Name
(2S)-3-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-diacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
Synonyms
N-α-Fmoc-O-β-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-L-serine; Fmoc-Ser(GlcNAc(Ac)3-β-D)-OH; Fmoc-L-Ser(beta-D-GlcNAc(Ac)3)-OH; (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(((2R,3R,4R,5S,6R)-3-acetamido-4,5-diacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)propanoic acid; O-(2-Acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-N-Fmoc-L-serine; N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-O-[3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl]-L-serine
Appearance
White to Off-white Solid
Purity
≥95% by HPLC
Density
1.39±0.1 g/cm3 (Predicted)
Melting Point
223-225°C (dec.)
Boiling Point
856.8±65.0°C (Predicted)
Storage
Store at -20°C
Solubility
Soluble in DMSO (Slightly), Methanol (Slightly, Heated)
InChI
InChI=1S/C32H36N2O13/c1-16(35)33-27-29(46-19(4)38)28(45-18(3)37)26(15-42-17(2)36)47-31(27)43-14-25(30(39)40)34-32(41)44-13-24-22-11-7-5-9-20(22)21-10-6-8-12-23(21)24/h5-12,24-29,31H,13-15H2,1-4H3,(H,33,35)(H,34,41)(H,39,40)/t25-,26+,27+,28+,29+,31+/m0/s1
InChI Key
ORICVOOXZDVFIP-ILRBKQRBSA-N
Canonical SMILES
CC(=O)NC1C(C(C(OC1OCC(C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24)COC(=O)C)OC(=O)C)OC(=O)C
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
K P Ravindranathan Kartha, Robert A Field, Shona L Scheuerl, Ivone Carvalho 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. Lacosamide isothiocyanate-based agents: novel agents to target and identify lacosamide receptors
Rihe Liu, Simon J Gaskell, James P Stables, Steven W Cotten, Onrapak Reamtong, Ki Duk Park, Christophe Salomé, Claire Eyers, Pierre Morieux, Harold Kohn J Med Chem . 2009 Nov 12;52(21):6897-911. doi: 10.1021/jm9012054.
(R)-Lacosamide ((R)-2, (R)-N-benzyl 2-acetamido-3-methoxypropionamide) has recently gained regulatory approval for the treatment of partial-onset seizures in adults. Whole animal pharmacological studies have documented that (R)-2 function is unique. A robust strategy is advanced for the discovery of interacting proteins associated with function and toxicity of (R)-2 through the use of (R)-2 analogues, 3, which contain "affinity bait (AB)" and "chemical reporter (CR)" functional groups. In 3, covalent modification of the interacting proteins proceeds at the AB moiety, and detection or isolation of the selectively captured protein occurs through the bioorthogonal CR group upon reaction with an appropriate probe. We report the synthesis, pharmacological evaluation, and interrogation of the mouse soluble brain proteome using 3 where the AB group is an isothiocyanate moiety. One compound, (R)-N-(4-isothiocyanato)benzyl 2-acetamido-3-(prop-2-ynyloxy)propionamide ((R)-9), exhibited excellent seizure protection in mice, and like (R)-2, anticonvulsant activity principally resided in the (R)-stereoisomer. Several proteins were preferentially labeled by (R)-9 compared with (S)-9, including collapsin response mediator protein 2.
3. Synthesis of a glycotripeptide and a glycosomatostatin containing the 3-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-L-serine residue
R Saltman, S Lavielle, N C Ling, R C Guillemin Carbohydr Res . 1981 Mar 2;89(2):229-36. doi: 10.1016/s0008-6215(00)85248-9.
3-O-(2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranosyl)-N- (tert-butyloxycarbonyl)-L-serine was synthesized and condensed by the solid-phase procedure to give the sequence Gly-[beta-D-GlcpNAc-(1 leads to 3)-Ser]-Ala-OH and beta-D-GlcpNAc-(1 leads to 3)-Ser-13-somatostatin. The synthetic glycopeptides appeared homogeneous on t.l.c. and l.c. examination and showed the correct amino acid composition and 2-amino-2-deoxy-D-glucose content. The structure of Gly-[beta-D-GlcpNAc-(1 leads to 3)-Ser]-Ala-OH was further confirmed by mass spectrometry of the N-acetyl permethyl derivative, and by n.m.r. spectroscopy.
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