D-.alpha.-Glutamine, N2-[N-(N-acetyl-.beta.-allo-muramoyl)-L-alanyl]-

Base Information

• Chemical Name: D-.alpha.-Glutamine, N2-[N-(N-acetyl-.beta.-allo-muramoyl)-L-alanyl]-
• CAS No.: 87420-48-2
• Molecular Formula: C₁₉H₃₂N₄O₁₁
• Molecular Weight: 492.483

Synonyms:

Chemical Property of D-.alpha.-Glutamine, N2-[N-(N-acetyl-.beta.-allo-muramoyl)-L-alanyl]-

Chemical Property:

• Boiling Point: 1023.7°Cat760mmHg
• Flash Point: 572.9°C
• Density: 1.45g/cm³

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of D-.alpha.-Glutamine, N2-[N-(N-acetyl-.beta.-allo-muramoyl)-L-alanyl]-

There total 34 articles about D-.alpha.-Glutamine, N2-[N-(N-acetyl-.beta.-allo-muramoyl)-L-alanyl]- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.9%

(R)-4-{(S)-2-[(R)-2-((2R,4aR,7R,8R,8aS)-7-Acetylamino-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-propionylamino]-propionylamino}-4-carbamoyl-butyric acid benzyl ester (87173-14-6) → muramyl dipeptide (56772-92-0,56816-15-0,74311-89-0,80953-11-3,87420-46-0,87420-47-1,87420-48-2,87420-49-3,87420-50-6,87420-93-7,53678-77-6)

Guidance literature:

With hydrogen; acetic acid; palladium on activated charcoal;

DOI:10.1021/jm00366a014

Reference yield: 85.4%

benzyl N2-(N-acetyl-1-O-benzyl-4,6-O-benzylidene-α-D-muramoyl)-L-alanyl-D-isoglutaminate (59573-84-1) → muramyl dipeptide (56772-92-0,56816-15-0,74311-89-0,80953-11-3,87420-46-0,87420-47-1,87420-48-2,87420-49-3,87420-50-6,87420-93-7,53678-77-6)

Guidance literature:

With hydrogen; acetic acid; palladium; In methanol; for 3h; Ambient temperature;

DOI:10.1246/bcsj.53.2570

Reference yield: 50.0%

N-acetyl-1-O-benzyl-4,6-O-benzylidenemuramoyl-L-alanyl-D-idoglutamine benzyl ester (93218-76-9) → muramyl dipeptide (56772-92-0,56816-15-0,74311-89-0,80953-11-3,87420-46-0,87420-47-1,87420-48-2,87420-49-3,87420-50-6,87420-93-7,53678-77-6)

Guidance literature:

With hydrogen; palladium; In acetic acid; for 96h;

DOI:10.1016/0008-6215(84)85224-6

upstream raw materials:

benzyl N²-(N-acetyl-1-O-benzyl-4,6-O-benzylidene-α-D-muramoyl)-L-alanyl-D-isoglutaminate

N-acetyl-1-O-benzyl-4,6-O-benzylidenemuramoyl-L-alanyl-D-idoglutamine benzyl ester

(R)-4-{(S)-2-[(R)-2-((2R,4aR,7R,8R,8aS)-7-Acetylamino-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-propionylamino]-propionylamino}-4-carbamoyl-butyric acid benzyl ester

benzyl (R)-5-amino-4-((tert-butoxycarbonyl)amino)-5-oxopentanoate

Downstream raw materials:

C₄₂H₄₂N₈O₁₇^(2-)*2Na⁽¹⁺⁾

(R)-2-(((3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl)oxy)propanoic acid

L-alanyl-D-isoglutamine

Refernces

ω-AMINOALKYL β-GLYCOSIDES OF N-ACETYLMURAMYL-L-ALANYL-D-ISOGLUTAMINE, AND THEIR CONJUGATES WITH MENINGOCOCCAL GROUP C POLYSACCHARIDE

10.1016/0008-6215(83)88218-4

The research focuses on the synthesis of w-aminoalkyl β-glycosides of N-acetylmuramyl-L-alanyl-D-isoglutamine (MDP) and their conjugates with meningococcal group C polysaccharide, aiming to enhance the immunogenicity of the polysaccharide antigen. Key chemicals involved in the study include 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyrano)-[2,1-d]-2-oxazoline, 6-(benzyloxycarbonylamino)-1-hexanol, L-alanyl-D-isoglutamine benzyl ester hydrochloride, and N-hydroxysuccinimide. The researchers synthesized the 6-aminohexyl β-glycoside of MDP and its spacer-arm-linked analog (3.8 nm) and coupled these with meningococcal group C polysaccharide. The resulting conjugates exhibited enhanced antigenicity in vitro but did not show enhanced immunogenicity in vivo.

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