18814-49-8

Usage

Uses

Used in Pharmaceutical Research and Development:
BOC-ALA-D-GLU(OBZL)-NH2 is used as a key component in peptide synthesis for the development of new drugs. Its unique structure allows for the creation of complex peptide chains that can be tailored to target specific biological pathways and diseases.
Used in Drug Discovery:
BOC-ALA-D-GLU(OBZL)-NH2 is utilized as a building block in the design and synthesis of novel peptide-based therapeutics. Its versatility in forming peptide bonds and the ability to incorporate various protecting groups make it an essential tool in drug discovery, enabling the development of innovative treatments for a wide range of medical conditions.
Used in Peptide Synthesis:
In the field of organic chemistry, BOC-ALA-D-GLU(OBZL)-NH2 is used as a precursor in the synthesis of various peptides. Its presence of both protecting groups and amino acids allows for the controlled assembly of peptide sequences, facilitating the production of specific bioactive peptides for research and therapeutic applications.
Used in Biochemistry and Molecular Biology:
BOC-ALA-D-GLU(OBZL)-NH2 is employed as a reagent in biochemical and molecular biology research. Its role in peptide synthesis aids in the study of protein structure, function, and interactions, contributing to a deeper understanding of biological processes and the development of targeted therapies.

Upstream product

• 15761-38-3 L-N-Boc-Ala 
• 18800-75-4 D-γ-methyl isoglutamine hydrochloride 
• 53759-36-7 γ-benzyl tert-butoxycarbonyl-L-alanyl-D-glutamate 
• 18800-73-2 benzyl (R)-5-amino-4-((tert-butoxycarbonyl)amino)-5-oxopentanoate 
• 6893-26-1 D-Glutamic acid 
• 18800-76-5 Boc-D-Glu(OBzl)-OSu 
• 100-51-6 benzyl alcohol 
• 80143-17-5 (R)-1-amino-5-(benzyloxy)-1,5-dioxopentan-2-aminium 2,2,2-trifluoroacetate 
• 3392-05-0 Boc-Ala-O-N-hydroxysuccinimide 
• 55297-72-8 (R)-5-amino-4-((tert-butoxycarbonyl)amino)-5-oxopentanoic acid 
• 19522-39-5 (R)-5-amino-4-(((benzyloxy)carbonyl)amino)-5-oxopentanoic acid 
• 63648-73-7 N-benzyloxycarbonyl-D-glutamic acid 
• 63648-75-9 D-isoglutamine hydrobromide 
• 2483-49-0 tert-butyloxycarbonyl-L-alanine p-nitrophenyl ester 

Downstream Products

• 62853-36-5 L-alanyl-(γ-benzyl ester D-isoglutamine) 
• 18814-50-1 (R)-5-amino-4-{(S)-2-[(tert-butoxycarbonyl)amino]propanamido}-5-oxopentanoic acid 
• 59524-62-8 L-alanyl-D-isoglutamine benzyl ester hydrochloride 
• 66025-93-2 (S)-1-(((R)-1-amino-5-(benzyloxy)-1,5-dioxopentan-2-yl)amino)-1-oxopropan-2-aminium 2,2,2-trifluoroacetate 
• 56772-92-0 muramyl dipeptide 
• 45159-25-9 L-alanyl-D-isoglutamine 
• 76379-21-0 (R)-4-{(S)-2-[(R)-2-((4aR,6S,7R,8R,8aS)-7-Acetylamino-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-4-methyl-pentanoylamino]-propionylamino}-4-carbamoyl-butyric acid benzyl ester 
• 66112-14-9 (R)-4-((S)-2-{(R)-2-[(4aR,6S,7R,8R,8aS)-6-Benzyloxy-7-(2-benzyloxy-acetylamino)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-propionylamino}-propionylamino)-4-carbamoyl-butyric acid benzyl ester 
• 76420-28-5 N-acetyl-1-O-benzyl-4,6-O-benzylidene-α-isomuramyl-L-alanyl-D-isoglutamine benzyl ester 
• 93218-76-9 N-acetyl-1-O-benzyl-4,6-O-benzylidenemuramoyl-L-alanyl-D-idoglutamine benzyl ester 
• 1332360-39-0 benzyl (4R)-5-amino-5-oxo-4-[((2S)-2-{[5-(1,1,3-trioxo-1,3-dihydro-2H-1,2-benzisothiazol-2-yl)pentanoyl]amino}propanoyl)amino]pentanoate 
• 1332360-40-3 benzyl (4R)-5-amino-5-oxo-4-[((2S)-2-{[4-(1,1,3-trioxo-1,3-dihydro-2H-1,2-benzisothiazol-2-yl)butanoyl]amino}propanoyl)amino]pentanoate 
• 1332360-41-4 benzyl (4R)-5-amino-5-oxo-4-{[(2S)-2-({2-[2-(1,1,3-trioxo-1,3-dihydro-2H-1,2-benzisothiazol-2-yl)ethoxy]acetyl}amino)propanoyl]amino}pentanoate 
• 1332360-42-5 benzyl (4R)-5-amino-4-[(2S)-2-{[(5,5-dioxo-5,7,8,9-tetrahydro-5λ6-pyrido[1,2-b][1,2]benzisothiazol-10-yl)carbonyl]amino}propanoylamino]-5-oxopentanoate 

Relevant academic research and scientific papers

Synthesis of Carbapenems Containing Peptidoglycan Mimetics and Inhibition of the Cross-Linking Activity of a Transpeptidase of l,d Specificity

The carbapenem class of β-lactams has been optimized against Gram-negative bacteria producing extended-spectrum β-lactamases by introducing substituents at position C2. Carbapenems are currently investigated for the treatment of tuberculosis as these drugs are potent covalent inhibitors of l,d-transpeptidases involved in mycobacterial cell wall assembly. The optimization of carbapenems for inactivation of these unusual targets is sought herein by exploiting the nucleophilicity of the C8 hydroxyl group to introduce chemical diversity. As β-lactams are structure analogs of peptidoglycan precursors, the substituents were chosen to increase similarity between the drug and the substrate. Fourteen peptido-carbapenems were efficiently synthesized. They were more effective than the reference drug, meropenem, owing to the positive impact of a phenethylthio substituent introduced at position C2 but the peptidomimetics added at position C8 did not further improve the activity. Thus, position C8 can be modified to modulate the pharmacokinetic properties of highly efficient carbapenems.

Synthesis of Bacterial-Derived Peptidoglycan Cross-Linked Fragments

Peptidoglycan (PG) is the core structural motif of the bacterial cell wall. Fragments released from the PG serve as fundamental recognition elements for the immune system. The structure of the PG, however, encompasses a variety of chemical modifications among different bacterial species. Here, the applicability of organic synthetic methods to address this chemical diversity is explored, and the synthesis of cross-linked PG fragments, carrying biologically relevant amino acid modifications and peptide cross-linkages, is presented using solution and solid phase approaches.

Further Insights on Structural Modifications of Muramyl Dipeptides to Study the Human NOD2 Stimulating Activity

A series of muramyl dipeptide (MDP) analogues with structural modifications at the C4 position of MurNAc and on the d-iso-glutamine (isoGln) residue of the peptide part were synthesized. The C4-diversification of MurNAc was conveniently achieved by using CuAAC click strategy to conjugate an azido muramyl dipeptide precursor with structurally diverse alkynes. d-Glutamic acid (Glu), replaced with isoGln, was applied for the structural diversity through esterification or amidation of the carboxylic acid. In total, 26 MDP analogues were synthesized and bio-evaluated for the study of human NOD2 stimulation activity in the innate immune response. Interestingly, MDP derivatives with an ester moiety are found to be more potent than reference compound MDP itself or MDP analogues containing an amide moiety. Among the varied lengths of the alkyl chain in ester derivatives, the MDP analogue bearing the d-glutamate dodecyl (C12) ester moiety showed the best NOD2 stimulation potency.

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.

Convergent synthesis of novel muramyl dipeptide analogues: Inhibition of porphyromonas gingivalis-induced pro-inflammatory effects by high doses of muramyl dipeptide

Porphyromonas gingivalis (P.g.)-induced TNF-α can be affected by muramyl dipeptide (MDP) in a biphasic concentration-dependent manner. We found that in P.g.-exposed macrophages, treatment with 10 μg/mL of MDP (MDP-low) up-regulated TNF-α by 29%, while 100

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.

Activation for catalysis of penicillin-binding protein 2a from methicillin-resistant Staphylococcus aureus by bacterial cell wall

Methicillin-resistant Staphylococcus aureus (MRSA) has acquired a unique penicillin-binding protein (PBP), PBP 2a, which has rendered the organism resistant to the action of all available β-lactam antibiotics. The X-ray structure of PBP 2a shows the active site in a closed conformation, consistent with resistance to inhibition by β-lactam antibiotics. However, it is known that PBP 2a avidly cross-links the S. aureus cell wall, which is its physiological function. It is shown herein that synthetic fragments of the bacterial cell wall bind in a saturable manner to PBP 2a and cause a conformational change in the protein that makes the active site more accessible to binding to a β-lactam antibiotic. These observations and measurements point to a novel strategy by nature to keep the active site of PBP 2a sheltered from the inhibitory activity of the antibiotics, yet it becomes available to the polymeric cell wall by a requisite conformational change for the critical cell wall cross-linking reaction. Copyright

Synthesis of γ-benzyl tert-butoxycarbonyl-L-alanyl-D-glutamate and its derivatives

A convenient method of obtaining Boc-L-Ala-D-iGln-OBzl and its amide analogs by condensing the N-hydroxysuccinimidyl ester of Boc-L-Ala with the γ-benzyl ester of D-Glu in the presence of NaHCO3, followed by amidation of the resulting Boc-L-Ala-D-Glu-γ-OBzl, is proposed. The use of l-adamantylamine and octadecylamine as amino components has enabled the corresponding α-adamantylamide and octadecylamide of the dipeptide to be obtained.