4229-38-3

Basic information

• Product Name: 2-ACETAMIDO-1-AMINO-1,2-DIDEOXY-B-D-GLUC OPYRANOSE
• Synonyms: 2-acetamido-1-amino-1,2-dideoxy-B-D-*glucopyranos;2-Acetamido-2-deoxy--D-glucosylamine;2-acetamido-1-amino-1,2-dideoxy-beta-D-glucopyranose;2-Acetamido-1-amino-1,2-dideoxy-β-D-glucopyranose;N-Acetyl-D-glucosylamine;2-Acetamido-2-deoxy-beta-D-glucopyranosylamine 97% (HPLC);2-ACETAMIDO-1-AMINO-1,2-DIDEOXY-B-D-GLUC OPYRANOSE;N-[(2R,3R,4R,5S,6R)-2-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS NO: 4229-38-3
• Molecular Formula: C₈H₁₆N₂O₅
• Molecular Weight: 220.22304
• Product Categories: Carbohydrates & Derivatives
• Mol File: 4229-38-3.mol
• Article Data: 32

Chemical Properties

• Melting Point: 103-112°C dec.
• Boiling Point: 556.2 °C at 760 mmHg
• Flash Point: 290.2 °C
• Appearance: /
• Density: 1.43g/cm³
• Vapor Pressure: 1.09E-14mmHg at 25°C
• Refractive Index: 1.576
• Storage Temp.: −20°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 13.15±0.70(Predicted)
• Stability: Moisture Sensitive
• CAS DataBase Reference: 2-ACETAMIDO-1-AMINO-1,2-DIDEOXY-B-D-GLUC OPYRANOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-ACETAMIDO-1-AMINO-1,2-DIDEOXY-B-D-GLUC OPYRANOSE(4229-38-3)
• EPA Substance Registry System: 2-ACETAMIDO-1-AMINO-1,2-DIDEOXY-B-D-GLUC OPYRANOSE(4229-38-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 4229-38-3(Hazardous Substances Data)

Usage

Description

2-ACETAMIDO-1-AMINO-1,2-DIDEOXY-B-D-GLUC OPYRANOSE, also known as 2-Acetamido-2-deoxy-β-D-glucosylamine, is a chemical compound that serves as a key intermediate in the synthesis of various 1-N-acyl derivatives. These derivatives are used to model the N-glycosylamine linkage found in glycoproteins. This brown solid is also utilized as a building block in a variety of synthetic reactions, making it a versatile compound in the field of chemistry.

Uses

1. Used in Pharmaceutical Industry:
2-ACETAMIDO-1-AMINO-1,2-DIDEOXY-B-D-GLUC OPYRANOSE is used as a synthetic intermediate for the development of 1-N-acyl derivatives that model the N-glycosylamine linkage of glycoproteins. This application is crucial in the study and development of new drugs targeting glycoprotein-related diseases.
2. Used in Chemical Synthesis:
2-ACETAMIDO-1-AMINO-1,2-DIDEOXY-B-D-GLUC OPYRANOSE is used as a building block in a variety of synthetic reactions across different industries. Its versatility as a synthetic building block allows for the creation of a wide range of chemical products, contributing to the advancement of various fields, including materials science, pharmaceuticals, and biotechnology.
3. Used in Research and Development:
2-ACETAMIDO-1-AMINO-1,2-DIDEOXY-B-D-GLUC OPYRANOSE is also employed in research and development settings, where it aids in the understanding of the structure and function of glycoproteins. This knowledge is essential for the development of novel therapeutic strategies and the advancement of scientific understanding in the field of glycobiology.

InChI:InChI=1/C8H16N2O5/c1-3(12)10-5-7(14)6(13)4(2-11)15-8(5)9/h4-8,11,13-14H,2,9H2,1H3,(H,10,12)/t4-,5+,6+,7+,8+/m0/s1

Upstream product

• 4239-72-9 ethyl 2-acetamido-3,4,6-tetra-O-acetyl-2-deoxy-1-thio-β-D-glucopyranoside 
• 10036-64-3 N-acetyl-D-glucosamine 
• 14131-63-6 D-glucosamine hydrochloride 
• 70749-28-9 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose 
• 824985-67-3 C₁₂H₁₉NO₈ 
• 6205-69-2 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl azide 
• 187879-61-4 ethyl thioglycoside 
• 165524-87-8 4-O-acetyl-1,5-anhydro-3,6-di-O-benzyl-2-deoxy-D-arabino-hex-1-enitol 
• 312967-20-7 ethyl 2-amino-2-deoxy-1-thio-β-D-glucopyranoside 
• 7512-17-6 N-Acetyl-D-glucosamine 
• 29847-23-2 2-N-acetylamido-2-deoxy-β-D-glucopyranosyl azide 
• 14131-68-1 N-acetyl-D-glucosamine 

Downstream Products

• 73982-43-1 2-acetamido-1-N-(bromoacetyl)-2-deoxy-β-D-glucopyranosylamine 
• 6216-46-2 2-acetamido-1-N--2-deoxy-β-D-glycopyranosylamine 
• 129785-93-9 (S)-2-[2-((S)-3-Acetylamino-2,5-dioxo-pyrrolidin-1-yl)-acetylamino]-3-phenyl-propionamide 
• 129785-97-3 (S)-2-Acetylamino-N⁴-((2R,3R,4R,5S,6R)-3-acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-N¹-[((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-methyl]-succinamide 
• 129785-96-2 (S)-1-[(S)-2-Acetylamino-3-((2R,3R,4R,5S,6R)-3-acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-ylcarbamoyl)-propionyl]-pyrrolidine-2-carboxylic acid ((S)-1-carbamoyl-2-phenyl-ethyl)-amide 
• 129785-94-0 (S)-2-{(S)-3-[(S)-2-Acetylamino-3-(4-hydroxy-phenyl)-propionylamino]-2,5-dioxo-pyrrolidin-1-yl}-4-methyl-pentanoic acid [(1S,2R)-1-((S)-1-carbamoyl-2-hydroxy-ethylcarbamoyl)-2-hydroxy-propyl]-amide 
• 129785-98-4 Ac-YN(GlcNAc)LTS-NH₂ 
• 16405-05-3 2-acetamido-1-N-(1-benzyloxy-N-benzyloxycarbonyl-4-L-aspartyl)-2-deoxy-β-D-glucopyranosylamine 
• 82155-29-1 2-acetamido-1-N--2-deoxy-β-D-glucopyranosylamine 
• 82155-28-0 2-acetamido-1-N--2-deoxy-β-D-glucopyranosylamine 
• 82155-28-0 2-acetamido-1-N--2-deoxy-β-D-glucopyranosylamine 
• 129785-95-1 Ac-Asn(β-D-GlcNHAc)-Val-Phe-NH2 
• 6205-72-7 1-N-acetyl-2-acetamido-2-deoxy-β-D-glucopyranosylamine 
• 333384-36-4 N-((2R,3R,4R,5S,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-2-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-acetamide 

Relevant articles and documents

Rapid glycoconjugation with glycosyl amines

Conjugation of unprotected carbohydrates to surfaces or probes by chemoselective ligation reactions is indispensable for the elucidation of their numerous biological functions. In particular, the reaction with oxyamines leading to the formation of carbohydrate oximes which are in equilibrium with cyclic N-glycosides (oxyamine ligation) has an enormous impact in the field. Although highly chemoselective, the reaction is rather slow. Here, we report that the oxyamine ligation is significantly accelerated without the need for a catalyst when starting with glycosyl amines. Reaction rates are increased up to 500-fold compared to the reaction of the reducing carbohydrate. For comparison, aniline-catalyzed oxyamine ligation is only increased 3.8-fold under the same conditions. Glycosyl amines from mono- and oligosaccharides are easily accessible from reducing carbohydrates via the corresponding azides by using Shoda's reagent (2-chloro-1,3-dimethylimidazolinium chloride, DMC) and subsequent reduction. Furthermore, glycosyl amines are readily obtained by enzymatic release from N-glycoproteins making the method suited for glycomic analysis of these glycoconjugates which we demonstrate employing RNase B. Oxyamine ligation of glycosyl amines can be carried out at close to neutral conditions which makes the procedure especially valuable for acid-sensitive oligosaccharides. This journal is

A Tripeptide Approach to the Solid-Phase Synthesis of Peptide Thioacids and N-Glycopeptides

A general and robust method for the incorporation of aspartates with a thioacid side chain into peptides has been developed. Pseudoproline tripeptides served as building blocks for the efficient fluorenylmethyloxycarbonyl (Fmoc) solid-phase synthesis of t

Convergent Synthesis of N-Linked Glycopeptides via Aminolysis of ω-Asp p-Nitrophenyl Thioesters in Solution

An efficient N-linked glycosylation reaction between glycosylamines and p-nitrophenyl thioester peptides has been developed. The reaction conditions are mild and compatible with the C-terminal free carboxylic acid group and the unprotected N-linked sialyl