17479-06-0

Basic information

• Product Name: uridine diphosphate galactosamine
• Synonyms: uridine diphosphate galactosamine;UDP-D-galactosamine
• CAS NO: 17479-06-0
• Molecular Formula: C₁₅H₂₅N₃O₁₆P₂
• Molecular Weight: 565.32
• Mol File: 17479-06-0.mol

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.93g/cm³
• Refractive Index: 1.671
• CAS DataBase Reference: uridine diphosphate galactosamine(CAS DataBase Reference)
• NIST Chemistry Reference: uridine diphosphate galactosamine(17479-06-0)
• EPA Substance Registry System: uridine diphosphate galactosamine(17479-06-0)

Safety Data

• Hazardous Substances Data: 17479-06-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Uridine diphosphate galactosamine is used as a key component in the synthesis of glycoproteins and glycolipids for various therapeutic applications. Its role in the regulation of protein function and cellular processes makes it a valuable compound in the development of new drugs and therapies.
Used in Biotechnology Industry:
Uridine diphosphate galactosamine is used as a vital substrate in the study and manipulation of protein glycosylation, which is crucial for understanding the molecular mechanisms underlying various biological processes. This knowledge can be applied to the development of novel biotechnological applications, such as the production of recombinant proteins with specific glycosylation patterns.
Used in Diagnostics:
Uridine diphosphate galactosamine is used as a diagnostic marker for certain diseases and conditions that involve alterations in glycosylation patterns. By measuring the levels or activity of enzymes related to UDP-GalNAc, researchers can gain insights into the pathophysiology of these diseases and develop new diagnostic tools.
Used in Research:
Uridine diphosphate galactosamine is used as a research tool to study the role of glycosylation in various biological processes, such as cell adhesion, embryo development, and immune response. This can help researchers understand the molecular mechanisms underlying these processes and identify potential targets for therapeutic intervention.

InChI:InChI=1/C15H25N3O16P2/c16-8-11(23)9(21)5(3-19)32-14(8)33-36(28,29)34-35(26,27)30-4-6-10(22)12(24)13(31-6)18-2-1-7(20)17-15(18)25/h1-2,5-6,8-14,19,21-24H,3-4,16H2,(H,26,27)(H,28,29)(H,17,20,25)/t5-,6-,8-,9+,10-,11-,12-,13-,14-/m1/s1

Upstream product

• 667462-08-0 2-trifluoroacetamido-2-deoxy-α,β-D-glucopyranose 
• 171032-74-9 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-glucopyranose 
• 537039-66-0 uridine 5'-diphospho-2-azido-2-deoxy-α-D-glucopyranoside 
• 2152-75-2 2-amino-2-deoxy-α-D-galactopyranosyl 1-phosphate 
• 58-97-9 5'-Uridylic Acid 
• 63-39-8 UTP 
• 90-76-6 2-deoxy-2-amino glucose 
• 35946-68-0 O³,O⁴,O⁶-triacetyl-2-amino-O¹-diphenoxyphosphoryl-2-deoxy-α-D-glucopyranose; hydrochloride 
• 212137-48-9 Phosphoric acid mono-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-hydroxymethyl-3-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-2-yl] ester 
• 28719-30-4 3,4,6-Tri-O-acetyl-2-trifluoracetamino-2-desoxy-D-glucose 
• 137766-83-7 2-deoxy-2-trifluoroacetamido-1,3,4,6-tetra-O-acetyl-α,β-D-glucopyranoside 
• 219564-51-9 3,4,6-tri-O-acetyl-2-deoxy-2-trifluoroacetylamino-α-D-glucopyranosyl dibenzyl phosphate 
• 212137-46-7 2-deoxy-2-[(trifluoroacetyl)amino]-D-glucopyranose-3,4,6-triacetate-1-(dihydrogen phosphate) 

Downstream Products

• 1338332-56-1 uridine 5'-diphospho-2-phenylacetamido-2-deoxy-α-D-glucopyranoside 
• 528-04-1 uridine-5'-diphospho-N-acetyl-D-galactosamine 
• 733810-59-8 C₆₄H₅₆Cl₂N₈O₂₂ 
• 528-04-1 uridine 5'-diphospho-N-acetylglucosamine 

Relevant articles and documents

Syntheses of unnatural N-substituted UDP-galactosamines as alternative substrates for N-acetylgalactosaminyl transferases

UDP-GalNAc analogues with slight modifications in the 2-acetamido group of the GalNAc moiety are prepared in order to study their role in the mechanism of the N-acetylgalactosaminyl transferase mediated glycosylation step. The analogues with N-propionyl-,

Chemoenzymatic Conjugation of Toxic Payloads to the Globally Conserved N-Glycan of Native mAbs Provides Homogeneous and Highly Efficacious Antibody-Drug Conjugates

A robust, generally applicable, nongenetic technology is presented to convert monoclonal antibodies into stable and homogeneous ADCs. Starting from a native (nonengineered) mAb, a chemoenzymatic protocol allows for the highly controlled attachment of any

Exploring the broad nucleotide triphosphate and sugar-1-phosphate specificity of thymidylyltransferase Cps23FL from: Streptococcus pneumonia serotype 23F

Glucose-1-phosphate thymidylyltransferase (Cps23FL) from Streptococcus pneumonia serotype 23F is the initial enzyme that catalyses the thymidylyl transfer reaction in prokaryotic deoxythymidine diphosphate-l-rhamnose (dTDP-Rha) biosynthetic pathway. In this study, the broad substrate specificity of Cps23FL towards six glucose-1-phosphates and nine nucleoside triphosphates as substrates was systematically explored, eventually providing access to nineteen sugar nucleotide analogs.

Chemoenzymatic Synthesis of Unnatural Nucleotide Sugars for Enzymatic Bioorthogonal Labeling

In recent years, the development of the enzymatic bioorthogonal labeling strategy has offered exciting possibilities in the probing of structure-defined glycan epitopes. This strategy takes advantage of relaxed donor specificity and strict acceptor specificity of glycosyltransferases to label target glycan epitopes with bioorthogonal reactive groups carried by unnatural nucleotide sugars in vitro. The subsequent covalent conjugation by bioorthogonal chemical reactions with either fluorescent or affinity tags allows further visualization, quantification, or enrichment of target glycan epitopes. However, the application and development of the enzymatic labeling strategy have been hindered due to the limited availability of unnatural nucleotide sugars. Herein, a platform that combines chemical synthesis and enzymatic synthesis for the facile preparation of unnatural nucleotide sugars modified with diverse bioorthogonal reactive groups is described. By this platform, a total of 25 UDP-GlcNAc and UDP-GalNAc derivatives, including the most well explored bioorthogonal functional groups, were successfully synthesized. Furthermore, the potential application of these compounds for use in enzymatic bioorthogonal labeling reactions was also evaluated.

PROCESS FOR THE CYCLOADDITION OF A HALOGENATED 1,3-DIPOLE COMPOUND WITH A (HETERO)CYCLOALKYNE

The present invention relates to a cycloaddition process comprising the step of reacting a halogenated aliphatic 1,3-dipole compound with a (hetero)cycloalkyne according to Formula (1): Preferably, the (hetero)cycloalkyne according to Formula (1) is a (he

PROCESS FOR THE CYCLOADDITION OF A HETERO(ARYL) 1,3-DIPOLE COMPOUND WITH A (HETERO)CYCLOALKYNE

A process is provided, comprising reacting a (hetero)aryl 1,3-dipole compound with a (hetero)cycloalkyne, wherein the (hetero)aryl 1,3-dipole compound comprises a 1,3-dipole functional group bonded to a (hetero)aryl group, and wherein the (hetero)aryl 1,3-dipole compound is a (hetero)aryl azide or a (hetero)aryl diazo compound; wherein: (i) the (hetero)aryl group of the (hetero)aryl 1,3-dipole compound comprises a substituent (ii) the (hetero)aryl group of the (hetero)aryl 1,3-dipole compound is an electron-poor (hetero)aryl group and wherein the (hetero)cycloalkyne is a (hetero)cyclooctyne or a (hetero)cyclononyne according to Formula (1). The invention also relates to the products obtainable by the process according to the invention.

PROCESS FOR THE MODIFICATION OF A GLYCOPROTEIN USING A ΒETA-(1,4)-N-ACETYLGALACTOSAMINYLTRANSFERASE OR A MUTANT THEREOF

The present invention relates to a process for the modification of a glycoprotein, using a β-(1,4)-N-acetylgalactosaminyltransferase or a mutant thereof.The process comprisesthe step of contacting a glycoprotein comprising a glycan comprising a terminal GlcNAc-moiety, in the presence of a β-(1,4)-N-acetylgalactosaminyl- transferase or a mutant thereof, with anon-natural sugar-derivative nucleotide.The non-natural sugar-derivative nucleotideis according to formula (3), wherein A is selected from the group consisting of -N3; -C(0)R3; -C=C-R4; -SH; -SC(0)R8; -SC(V)OR8, wherein V is O or S; -X wherein X is selected from the group consisting of F, CI, Br and I; -OS(0)2R5; an optionally substituted C2 - C24 alkyl group; an optionally substituted terminal C2 - C24 alkenyl group; and an optionally substituted terminal C3 - C24 allenyl group.

SULFAMIDE LINKER, CONJUGATES THEREOF, AND METHODS OF PREPARATION

The present invention relates to a compound comprising an alpha-end and an omega-end, the compound comprising on the alpha-end a reactive group Qlcapable of reacting with a functional group F1present on a biomolecule and on the omega-end a target molecule, the compound further comprising a group according to formula (1) or a salt thereof: Said compound may also be referred to as a linker-conjugate. The invention also relates to a process for the preparation of a bioconjugate, the process comprising the step of reacting a reactive group Q1of a linker-conjugate according to the invention with a functional group F1of a biomolecule. The invention further relates to a bioconjugate obtainable by the process according to the invention. In a preferred embodiment, the invention concerns a process for the preparation of a bioconjugate via a cycloaddition, such as a (4+2)-cycloaddition (e.g. a Diels-Alder reaction) or a (3+2)-cycloaddition (e.g. a 1,3-dipolar cycloaddition).

Compositions and methods for the transfer of a hexosamine to a modified nucleotide in a nucleic acid

Nucleic acids comprising β-glucosaminyloxy-5-methylcytosine; compositions, kits and methods of producing the nucleic acids using a glycosyltransferase; and methods of using the nucleic acids are described.

PROCESS FOR THE CYCLOADDITION OF A HALOGENATED 1,3-DIPOLE COMPOUND WITH A (HETERO)CYCLOALKYNE

The present invention relates to a cycloaddition process comprising the step of reacting a halogenated aliphatic 1,3-dipole compound with a (hetero)cycloalkyne according to Formula (1): Preferably, the (hetero)cycloalkyne according to Formula (1) is a (he