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

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

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

L-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

Specification
Reference Reading

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.