79640-72-5

Basic information

• Product Name: H-Glu(OMe)-OtBu
• Synonyms: (S)-1-tert-Butyl 5-methyl 2-aminopentanedioate;L-Glutamic acid, 1-(1,1-dimethylethyl) 5-methyl ester
• CAS NO: 79640-72-5
• Molecular Formula: C₁₀H₁₉NO₄
• Molecular Weight: 217.26216
• Mol File: 79640-72-5.mol

Chemical Properties

• Appearance: /
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• CAS DataBase Reference: H-Glu(OMe)-OtBu(CAS DataBase Reference)
• NIST Chemistry Reference: H-Glu(OMe)-OtBu(79640-72-5)
• EPA Substance Registry System: H-Glu(OMe)-OtBu(79640-72-5)

Safety Data

• Hazardous Substances Data: 79640-72-5(Hazardous Substances Data)

Usage

Uses

Used in Peptide Synthesis:
H-Glu(OMe)-OtBu serves as a building block in peptide synthesis, contributing to the formation of complex peptide structures. Its presence facilitates the process by providing a stable and protected intermediate, which is essential for the successful synthesis of peptides.
Used in Organic Synthesis as a Protective Group:
In organic synthesis, H-Glu(OMe)-OtBu is utilized as a protective group to shield functional groups from unwanted reactions. This protection is crucial for maintaining the integrity of the compound during multi-step synthesis processes, ensuring the desired end product is achieved without unwanted side reactions.
Used in Pharmaceutical Industry:
H-Glu(OMe)-OtBu is employed in the pharmaceutical industry for the production of various compounds and drugs. Its stability and reactivity make it suitable for the development of new pharmaceutical agents, potentially leading to advancements in medicine and treatment options.
Used in Biotechnology Industry:
In the biotechnology sector, H-Glu(OMe)-OtBu is used for the production of bioactive compounds and therapeutic agents. Its role in creating stable and functional molecules supports the development of innovative biotechnological products that can address various health and environmental challenges.

Upstream product

• 540-88-5 acetic acid tert-butyl ester 
• 1499-55-4 L-glutamic acid 5-methyl ester 
• 4652-65-7 (S)-2-Benzyloxycarbonylamino-pentanedioic acid 5-methyl ester 
• 115-11-7 isobutene 
• 57732-63-5 1-tert-butyl 5-methyl (2S)-2-{[(benzyloxy)carbonyl]amino}pentanedioate 
• 3077-51-8 γ-methyl L-glutamate hydrochloride 
• 367275-86-3 1,1-dimethylethyl 5-methyl N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-glutamate 
• 212121-62-5 1-tert-butyl 5-methyl (S)-2-((diphenylmethylene)amino)pentanedioate 
• 81477-94-3 N-(diphenylmethylene)glycine tert-butyl ester 
• 84793-07-7 Fmoc-Glu-OtBu 
• 226900-42-1 1-(tert-butyl) 5-methyl 2-[(diphenylmethylene)amino]pentanedioate 
• 56-86-0 L-glutamic acid 
• 1155-62-0 N-benzyloxycarbonyl-L-glutamic acid 
• 4124-76-9 N-(benzyloxycarbonyl)-L-glutamic acid anhydride 

Downstream Products

• 23736-78-9 N-(benzyloxycarbonyl)-γ-L-glutamyl-L-glutamic acid, α,α'-di-tert-butyl γ-methyl triester 
• 79648-88-7 α-tert-butyl γ-methyl N'-<4--N-methylamino>benzoyl>-L-glutamate 
• 133042-41-8 α-tert-butyl γ-methyl N-(4-nitrobenzoyl)-L-glutamate 
• 130761-69-2 1-tert-butyl-N²-(3,5-dinitrobenzoyl)-L-glutamic acid 5-methyl ester 
• 118545-50-9 α-tert-butyl γ-methyl N-trityl-L-glutamate 
• 79640-70-3 (S)-5-(tert-butoxy)-4-(4-(((2,4-diaminopteridin-6-yl)methyl)(methyl)amino)benzamido)-5-oxopentanoic acid 
• 67022-39-3 γ-methyl N'-<4--N-methylamino>benzoyl>-L-glutamate 
• 181040-47-1 N^α-[[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-(α-tert-butoxy)glutamoyl]-N-[2-hydroxy-1,1-bis(hydroxymethyl)ethyl]glycinamide 
• 511544-99-3 N^α-[[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-(α-tert-butoxy)glutamoyl]-N-[1,1-bis(hydroxymethyl)-2-[(1-oxohexadecyl)oxy]ethyl]glycinamide 
• 181040-49-3 N^α-[[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-(α-tert-butoxy)glutamoyl]-N-[1-hydroxymethyl-2-[(1-oxohexadecyl)oxy]-1-[(1-oxohexadecyl)oxymethyl]ethyl]glycinamide 
• 181040-33-5 N^α-[[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-(α-tert-butoxy)glutamoyl]-N-[2-[(1-oxohexadecyl)oxy]-1,1-bis[[(1-oxohexadecyl)oxy]methyl]ethyl]glycinamide 
• 56-87-1 L-lysine 
• 91229-86-6 tert-butyl (S)-2-<(tert-butyloxycarbonyl)amino>-5-bromopentanoate 
• 2812-46-6 proline tert-butyl ester 

Relevant articles and documents

Efficient Synthesis of a Family of Bifunctional Chelators Based on the PCTA[12] Macrocycle Suitable for Bioconjugation

PCTA[12] is a 12-membered tetraaza-macrocyclic ligand that incorporates a pyridine unit within the macrocyclic ring and three acetate pendant arms. Unlike DOTA and NOTA chelators, PCTA is a recent entry to the field of macrocyclic polyaminocarboxylate ligands available to complex a variety of M2+/M3+ ions for biomedical applications such as diagnostic and radiotherapeutic. Despite the promising properties of its chelates, only a few of bifunctional chelating agents (BFCAs) derived from PCTA have been described so far. Based on our very recent methodology for the preparation of PCTA[12] itself, we report here the efficient synthesis of several BFCAs derived from PCTA bearing a free reactive function group, mainly devoted to conjugation purposes: ester, carboxylic acid, alcohol, aliphatic amine, aromatic amine, maleimide, bromo or azide functions. These functions were introduced either on the 4-position of the pyridine ring or on the methylene carbon atom of the central acetate chelating arm, while keeping the three carboxylate groups available for metal chelation. Moreover, two of these BFCAs-PCTA were used for conjugation with a tetrapeptide (cholecystokinin analogue), a bioactive molecule (biotin), or a solid support (silica gel).

Synthesis of ortho-carboranyl derivatives of (S)-asparagine and (S)-glutamine

(S)-Asparagine and (S)-glutamine ortho-carboranyl derivatives with free amino and carboxy groups in the α-position were synthesized. By an example of Nγ-(1,2-dicarba-closo-dodecarboran-3-yl)-(S)-glutamine it was demonstrated that the developed synthetic approach carboranyl derivatives of amino acids allowed the preparation of optically pure isomers.

Synthesis and evaluation of acyl protein thioesterase 1 (APT1) inhibitors

Lipid-modified proteins play decisive roles in important biological processes such as signal transduction, organisation of the cytoskeleton and vesicular transport. Lipidation of these proteins is essential for correct biological function. Among the modifications with lipids, prenylation and myristoylation are well understood. However, the machinery of palmitoylation is still under investigation. Recently, an enzyme, acyl protein thioesterase 1 (APT1), that may play a regulatory role in the palmitoylation cycle of HRas and G-protein a subunits, was purified. Motivated by this work, several inhibitors of APT1 were designed, synthesized and biologically evaluated leading to highly active compounds.

Synthesis of (ε-13C-,ε-15N)-enriched L-lysine - Establishing schemes for the preparation of all possible 13C and 15N isotopomers of L-lysine, L-ornithine, and L-proline

In this paper we describe a simple synthetic strategy that, with the right rational adaptation, gives direct access to any 13C/15N isotopomer of L-glutamate, L-ornithine, L-proline, L-lysine, and L-α, amino adipic acid. This strategy also allows access to nonproteinogenic amino acids like L-citrulline in high yields and optical purity. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Tight binding ligand approach to oligosaccharide-grafted protein

A novel type of artificial glycoprotein was developed, by using dihydrofolate reductase (DHFR) and methotrexate (MTX) as a protein-ligand pair. Various oligosaccharides linked to MTX were shown to bind tightly with DHFR and afforded oligosaccharide-grafted protein, which could be isolated easily by lectin beads.

Highly enantioselective synthesis of cyclic and functionalized α-amino acids by means of a chiral phase transfer catalyst

The chiral quaternary ammonium salt 1 serves as phase transfer catalyst for the enantioselective conversion of the glycine derivative 2 to a variety of cyclic and acyclic chiral α amino acids with enantioselectivities as high as 200:1 in alkylation and Michael addition reactions.

Folate-based inhibitors of thymidylate synthase: Synthesis and antitumor activity of γ-linked sterically hindered dipeptide analogues of 2-desamino- 2-methyl-N10-propargyl-5,8-dideazafolic acid (ICI 198583)

In an effort to synthesize inhibitors of thymidylate synthase (TS) that do not undergo polyglutamation, a series of γ-linked sterically hindered dipeptide analogues of 2-desamino-2-methyl-N10-propargyl-5,8-dideazafolic acid (ICI 198583) was pre

Total synthesis of the methanogenic cofactors methanofuran and methanofuran b

Methanofuran, 3-[p-((N-(N″-((4R,5S)- or (4S,5A)-4,5,7-tricarboxyheptanoyl)-γL-glutamyl-γ-L-glutamyl)-β- amino)ethyl]phenoxymethyl}-5-(aminomethyl)furan, and methanofuran b, 3-{p-[(N-(-γ-L-glutamyl-γ-L-glutamyl-γ-L-glutamyl-γ-L- glutamyl)-β-amino)ethyl]phenoxymethyl}-5-(aminomethyl)furan, are the first cofactors involved in the conversion of carbon dioxide to methane by the methanogenic bacteria Methanobacterium thermoautotrophicum and Methanosarcina barkeri, respectively. These two cofactors have now been synthesized, starting from glutamic acid, dimethyl glutarate, methyl 5-formyl-3-furoate, and tyramine. The synthetic compounds give the same NMR and mass spectra and biological activities as the natural cofactors.

Synthesis and Siderophore Activity of Albomycin-like Peptides Derived from N5-Acetyl-N5-hydroxy-L-ornithine

N5-Acetyl-N5-hydroxy-L-ornithine (1), the key constituent of several microbial siderophores, has been synthesized in 23percent yield overall from N-Cbz-L-glutamic acid 1-tert-butyl ester (6) derived from L-glutamic acid.Reduction of 6 to 7 and treatment with N-(trichloroethoxy)carbonyl>-O-benzylhydroxylamine (8), and diethyl azodicarboxylate and triphenylphosphine followed by deprotection produced the protected N5-acetyl-N5-hydroxy-L-ornithine derivatives 11 and 12 in large quantities (10-20 g).Following α-amino and α-carboxyl deprotections of 11 and 12, EEDQ mediated peptide coupling and final deprotection provided amino acid 1 and six albomycin-like peptides (20, 23, 25, 28, 35, and 36).The growth-promoting ability of each was evaluated with the siderophore biosynthesis mutant Shigella flexneri SA240 (SA 100 iucD:Tn5).These results indicate that substantial modification of the framework of peptide-based siderophores can be tolerated by microbial iron-transport systems.

Stereospecific Amino Acid Synthesis; Preparation of the γ-Anion derived from Glutamic Acid

Reaction of α-t-butyl γ-methyl N-trityl-L-glutamate (7) with lithium isopropylcyclohexylamide in hexane leads to the specific formation of the γ-ester enolate, a potential synthetic equivalent to the γ-anion synthon for stereospecific α-amino acid synthesis.