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Merck
CN

A6681

Sigma-Aldrich

2-Acetamido-1-N-(β-L-aspartyl)-2-deoxy-β-D-glucopyranosylamine

≥98%

Synonym(s):

β-D-GlcNAc-(1→N)-Asn, 2-Acetamido-1-β-(L-aspartamido)-1,2-dideoxy-D-glucose, L-Asparagine, N-[2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl]

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About This Item

Empirical Formula (Hill Notation):
C12H21N3O8
CAS Number:
2776-93-4
Molecular Weight:
335.31
MDL number:
MFCD00056071
UNSPSC Code:
12352201
PubChem Substance ID:
24891128
NACRES:
NA.25

Key Documents

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Assay

≥98%

form

powder

optical activity

[α]/D 22 to 26 °, c = 1% (w/v) in water

technique(s)

thin layer chromatography (TLC): suitable

storage temp.

−20°C

SMILES string

CC(=O)NC1C(O)C(O)C(CO)OC1NC(=O)CC(N)C(O)=O

InChI

1S/C12H21N3O8/c1-4(17)14-8-10(20)9(19)6(3-16)23-11(8)15-7(18)2-5(13)12(21)22/h5-6,8-11,16,19-20H,2-3,13H2,1H3,(H,14,17)(H,15,18)(H,21,22)

InChI key

YTTRPBWEMMPYSW-UHFFFAOYSA-N

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Application

n-acetylglucosaminylasparagine [2-Acetamido-1-N-(β-L-aspartyl)-2-deoxy-β-D-glucopyranosylamine] may be useful in studies on Aspartylglycosaminuria.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
098H3908
039H3911

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T Autti et al.
Acta radiologica (Stockholm, Sweden : 1987), 49(6), 687-692 (2008-06-24)
Aspartylglucosaminuria (AGU) is an autosomal recessive lysosomal disease caused by deficiency of aspartylglucosaminidase. A thalamic T2 signal intensity decrease is associated with lysosomal diseases. To investigate thalamic signal intensity in AGU by performing a retrospective review of brain magnetic resonance
J M Risley et al.
Journal of enzyme inhibition, 16(3), 269-274 (2001-11-08)
Glycosylasparaginase catalyzes the hydrolysis of the N-glycosylic bond between asparagine and N-acetylglucosamine in the catabolism of N-linked glycoproteins. Previously only three competitive inhibitors, one noncompetitive inhibitor, and one irreversible inhibitor of glycosylasparaginase activity had been reported. Using human glycosylasparaginase from
Ulla Dunder et al.
Journal of inherited metabolic disease, 33(5), 611-617 (2010-07-08)
Aspartylglycosaminuria (AGU) is a lysosomal storage disease caused by deficient activity of glycosylasparaginase (AGA), and characterized by motor and mental retardation. Enzyme replacement therapy (ERT) in adult AGU mice with AGA removes the accumulating substance aspartylglucosamine from and reverses pathology
A Schäfer et al.
Carbohydrate research, 313(2), 107-116 (1999-01-09)
The preparative synthesis of a new N4-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-L-asparagine mimetic 1, starting from 2-amino-1,5-anhydro-2-deoxy-glucitol hydrochloride and Z-Asp-(OH)-OBn is described. This glycosyl-amino acid unit 1 is expected to show higher stabilities towards in vivo conditions. Further, the use of 1 as building block
J Zlotogora et al.
Journal of inherited metabolic disease, 20(6), 799-802 (1998-01-14)
Aspartylglucosaminuria (AGU) is a rare disorder of glycoprotein metabolism caused by the deficiency of the lysosomal enzyme aspartylglucosaminidase (AGA). AGU is inherited as an autosomal recessive trait and occurs with a high frequency in Finland because of a founder effect.
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