2578-33-8

Basic information

• Product Name: H-D-GLU(OBZL)-OH
• Synonyms: H-D-GLU(OBZL)-OH;D-GAMMA-BENZYL GLUTAMATE;D-GLUTAMIC ACID GAMMA-BENZYL ESTER;D-GLUTAMIC ACID(OBZL)-OH;D-Glutamic acid γ-benzyl ester;H-D-Glu(Bzl)-OH;D-GLUTAMIC ACID-Y-BENZYLESTER;H-D-Glu(OBzl)-OH D-GlutaMic acid γ-benzyl ester
• CAS NO: 2578-33-8
• Molecular Formula: C₁₂H₁₅NO₄
• Molecular Weight: 237.25
• Product Categories: Amino Acid Derivatives;Amino Acids
• Mol File: 2578-33-8.mol
• Article Data: 12

Chemical Properties

• Melting Point: 176℃
• Boiling Point: 426.1 °C at 760 mmHg
• Flash Point: 211.5 °C
• Appearance: /
• Density: 1.245 g/cm³
• Vapor Pressure: 5.08E-08mmHg at 25°C
• Refractive Index: 1.555
• Storage Temp.: Store at RT.
• PKA: 2.20±0.10(Predicted)
• CAS DataBase Reference: H-D-GLU(OBZL)-OH(CAS DataBase Reference)
• NIST Chemistry Reference: H-D-GLU(OBZL)-OH(2578-33-8)
• EPA Substance Registry System: H-D-GLU(OBZL)-OH(2578-33-8)

Safety Data

• Hazardous Substances Data: 2578-33-8(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white powder

InChI:InChI=1/C12H15NO4/c13-10(12(15)16)6-7-11(14)17-8-9-4-2-1-3-5-9/h1-5,10H,6-8,13H2,(H,15,16)/t10-/m1/s1

Upstream product

• 6893-26-1 D-Glutamic acid 
• 98-11-3 benzenesulfonic acid 
• 100-51-6 benzyl alcohol 

Downstream Products

• 119598-29-7 N-(N-benzyloxycarbonyl-O-methyl-L-γ-glutamyl)-D-glutamic acid-5-benzyl ester-1-methyl ester 
• 59486-73-6 (2R)-5-(benzyloxy)-2-{[(benzyloxy)carbonyl]amino}-5-oxopentanoic acid 
• 5249-41-2 N-Formyl-D-glutaminsaeure-5-benzylester 
• 35793-73-8 N-(tert-butyloxycarbonyl)-γ-benzyl-D-glutamic acid 
• 53759-36-7 γ-benzyl tert-butoxycarbonyl-L-alanyl-D-glutamate 
• 104091-11-4 N-Fmoc-D-Glu γ-benzyl ester 
• 119598-29-7 N-(N-benzyloxycarbonyl-O-methyl-D-γ-glutamyl)-D-glutamic acid-5-benzyl ester-1-methyl ester 
• 945492-97-7 (2S)-2-[N-allyl-3-(4-benzyloxyphenyl)acetamido]-N-[(2R)-1-(N-allyl-o-nitrophenylsulfonamido)-5-triisopropylsilyloxypentan-2-yl]-5-triisopropylsilyloxypentanamide 
• 945493-02-7 (2R,5R,6E)-2,5-bis[3-(triisopropylsilyloxy)propyl]-1-[3-(4-benzyloxyphenyl)propionyl]-7-(o-nitrobenzenesulfonyl)-1,4,7-triazacycloundec-9-en-3-one 
• 945493-01-6 (2S,5R,6E)-2,5-bis[3-(triisopropylsilyloxy)propyl]-1-[3-(4-benzyloxyphenyl)propionyl]-7-(o-nitrobenzenesulfonyl)-1,4,7-triazacycloundec-9-en-3-one 
• 945493-06-1 (2R,5R,6E)-2,5-bis[3-(triisopropylsilyloxy)propyl]-1-(4-benzyloxyphenylacetyl)-7-(o-nitrobenzenesulfonyl)-1,4,7-triazacycloundec-9-en-3-one 
• 945493-05-0 (2S,5R,6E)-2,5-bis[3-(triisopropylsilyloxy)propyl]-1-(4-benzyloxyphenylacetyl)-7-(o-nitrobenzenesulfonyl)-1,4,7-triazacycloundec-9-en-3-one 

Relevant articles and documents

Design, synthesis, and biological evaluation of desmuramyl dipeptides modified by adamantyl-1,2,3-triazole

Muramyl dipeptide (MDP) is the smallest peptidoglycan fragment able to trigger the immune response. Structural modification of MDP can lead to the preparation of analogs with improved immunostimulant properties, including desmuramyl peptides (DMPs). The aim of this work was to prepare the desmuramyl peptide (L-Ala-D-Glu)-containing adamantyl-triazole moiety and its mannosylated derivative in order to study their immunomodulatory activities in vivo. The adjuvant activity of the prepared compounds was evaluated in a murine model using ovalbumin as an antigen, and compared to the reference adjuvant ManAdDMP. The results showed that the introduction of the lipophilic adamantyl-triazole moiety at the C-terminus of L-Ala-D-Glu contributes to the immunostimulant activity of DMP, and that mannosylation of DMP modified with adamantyl-triazole causes the amplification of its immunostimulant activity.

NOVEL MURAMYL PEPTIDE DERIVATIVE COMPOUND, SYNTHESIS AND USES THEREOF

The invention relates to novel Muramyl Dipeptide (MDP) derivative compound of structural Formula-VIII, a process for synthesis, intermediates used in the synthesis and use thereof. R = alkyl (both linear and branched), aryl, substituted aryl, alkoxy alkyl Wherein, R can be both linear and branched alkyl, aryl, substituted aryl and alkoxy alkyl. These compounds possess excellent pharmacological properties, in particular immunomodulating properties for use as adjuvant in vaccine formulations. These compounds are, particularly useful as adjuvants in vaccines.

Chemical synthesis and anti-tumor and anti-metastatic effects of dual functional conjugate

The present invention discloses chemical synthesis, anti-tumor and anti-metastatic effects of a dual functional conjugate as shown by formula I. Specifically, paclitaxel or docetaxol is linked with muramyl dipeptide derivative to form a conjugate, thus dual anti-tumor and anti-metastatic effects are achieved by combination of chemotherapy and immunotherapy. The present invention also discloses that paclitaxel or docetaxol and muramyl dipeptide derivative conjugate is synthesized by combination of solid-phase and solution-phase synthesis, and said conjugate can be used in manufacture of anti-tumor medicaments as proved by reliable bioassays.