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

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 
• 4419-48-1 N-(N-benzyloxycarbonyl-O-methyl-L-γ-glutamyl)-D-glutamic acid-1-methyl ester 
• 124227-53-8 N-(N-benzyloxycarbonyl-O-methyl-L-γ-glutamyl)-5-thio-D-glutamic acid-1-methyl ester-S-phenyl ester 
• 42929-62-4 (S)-5-(benzyloxy)-2-bromo-5-oxopentanoic acid 
• 65671-47-8 C₂₁H₃₀N₂O₇ 
• 1286246-27-2 Nα-[4-chlorocinnamoyl-L-alanyl-D-isoglutaminyl]-L-lysine 

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; wherein R1 and R2 both are hydrogen; or R1 is hydrogen and R2 is alkyl or aryl; or R1 is alkyl or aryl and R2 is hydrogen; or R1 and R2 both are alkyl or aryl (same or different groups); wherein alkyl group constitute C1-C6 alkyl or higher (both linear and branched) with or without heteroatoms; and aryl group constitute phenyl, substituted phenyl, heteraryl, arylalkyl and polynuclear aromatics. 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.

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 showed by formula I. In detail, 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.

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.

Solution-phase synthesis of a muramyl dipeptide analogue MDA

The solution-phase synthesis of a muramyl dipeptide (MDP) analogue of Nα-[4-chlorocinnamoyl-l-alanyl-d-isoglutaminyl]-l-lysine (MDA, 2) is reported that possesses the features of easy feasibility, safety and low cost in large scale of synthesis.

Design and synthesis of all diastereomers of cyclic pseudo-dipeptides as mimics of cyclic CXCR4 pentapeptide antagonists

The four diastereomers of 2,5-bis[(3-guanidino)propyl]-1-[3-(4- hydroxyphenyl)propionyl]-7-(2-naphthylacetyl)-1,4,7-triazacycloundec-9-en-3-one (54-57) and of 2,5-bis[(3-guanidino)propyl]-1-(4-hydroxyphenylacetyl)-7-(2- naphthylacetyl)-1,4,7-triazacycloundec-9-en-3-one (58-61) were synthesized by a divergent methodology from l- and d-glutamic acids. The 11-membered ring core was made by ring closing metathesis of linear bis(allylamines), and the guanidyl functions were introduced by a simultaneous double Mitsunobu reaction using bis(Boc)guanidine. These compounds were designed to mimic cyclic pentapeptide FC131 (c[Gly-d-Tyr-Arg-Arg-Nal]). The Royal Society of Chemistry.

Process for the preparation of omega-benzyl esters of amino diacids and of alkanesulphonates of these esters, and these alkanesulphonates

The invention relates to a process for the preparation of an ?-benzyl ester of an amino diacid, characterized in that the amino diacid is reacted with a benzyl alcohol derivative of formula (I) 1 in which the R1 substituent or substituents, which are identical or different, represent a hydrogen atom, a C1 to C4 alkyl group, a C1 to C4 alkoxy group or a halogen atom and n is equal to 1, 2 or 3, in the presence of at least one mol per mole of the amino diacid of an alkanesulphonic acid, optionally in the presence of a solvent. The intermediate alkanesulphonates of the ?-benzyl esters of amino diacids and the ?-benzyl esters of amino diacids are obtained with a good yield and an excellent purity by virtue of this process.

Solid-phase synthesis of muramyl dipeptide (MDP) derivatives using a multipin method

Solid-phase synthetic method of muramyl dipeptide derivatives is reported. A diverse library of muramyl dipeptides could be potentially synthesized by acylation, reductive alkylation, sulfonamide formation, urea formation, N-alkylation, amine addition, or component Ugi reactions based on this method for drug screening. (C) 2000 Elsevier Science Ltd. All rights reserved.

Synthesis of a radoilabeled type A cholecystokinin receptor antagonist, (R)-N-pentyl-N-(4,5-di[3H]pentyl)N(α)-(3-quinolinoyl)glutamic acid amide

A method for the preparation of a radiolabeled CCK(A)-specific antagonist, (R)-N-pentyl-N-(4,5-di[3H]pentyl)N(α)-(3-quinolinoyl)glutamic acid amide, [3H]-A-65186, is described. (R)-γ-Benzyl-N-BOC-glutamic acid was coupled with N-(4-pentenyl)-N-pentylamine using BOPCl and TEA in dichloromethane to provide the corresponding amide. Deprotection of the α-amino moiety followed by coupling with 3-quinolinecarboxylic acid in the presence of EDCI, TEA, and HOBt in dichloromethane resulted in (R)-N-(4-pentenyl)-N-pentyl γ-benzyl-N(α)-(3-quinolinoyl)glutamic acid amide. Tritiation with concomitant hydrogenolysis of the benzyl ester proceeds smoothly to provide [3H]-A-65186.