13574-13-5

Basic information

• Product Name: Boc-L-Glutamic acid 5-benzylester
• Synonyms: n-[(1,1-dimethylethoxy)carbonyl]-l-glutamicaci5-(phenylmethyl)ester;T-BUTYLOXYCARBONYL-L-GLUTAMIC ACID GAMMA-BENZYL ESTER;TBOC-L-GLUTAMIC ACID (OBZL);N-BOC-L-GLUTAMIC ACID 5-BENZYL ESTER;N-ALPHA-TERT-BUTYLOXYCARBONYL-L-GLUTAMIC ACID GAMMA-BENZYL ESTER;N-ALPHA-TERT-BOC-L-GLUTAMIC-GAMMA-BENZYL ESTER;N-ALPHA-T-BOC-L-GLUTAMIC ACID GAMMA-BENZYL ESTER;N-ALPHA-T-BUTOXYCARBONYL-L-GLUTAMIC ACID GAMMA-BENZYL ESTER
• CAS NO: 13574-13-5
• Molecular Formula: C₁₇H₂₃NO₆
• Molecular Weight: 337.36762
• EINECS: 237-007-5
• Product Categories: Amino Acids;Glutamic acid [Glu, E];Boc-Amino Acids and Derivative;Amino Acids (N-Protected);Biochemistry;Boc-Amino Acids;Boc-Amino acid series
• Mol File: 13574-13-5.mol

Chemical Properties

• Melting Point: 69-71 °C
• Boiling Point: 473.68°C (rough estimate)
• Flash Point: 269.9 °C
• Appearance: white to off-white powder
• Density: 1.1452 (rough estimate)
• Vapor Pressure: 9.49E-12mmHg at 25°C
• Refractive Index: -16.5 ° (C=2, DMF)
• Storage Temp.: 2-8°C
• Solubility: Soluble in N,N- Dimethyl formamide.
• PKA: 3.81±0.10(Predicted)
• BRN: 2226572
• CAS DataBase Reference: Boc-L-Glutamic acid 5-benzylester(CAS DataBase Reference)
• NIST Chemistry Reference: Boc-L-Glutamic acid 5-benzylester(13574-13-5)
• EPA Substance Registry System: Boc-L-Glutamic acid 5-benzylester(13574-13-5)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 13574-13-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Boc-L-Glutamic acid 5-benzylester is used as a pharmaceutical intermediate for the synthesis of various drugs. Its application is primarily due to its unique chemical properties, which allow it to be a key component in the development of new medications.
As a pharmaceutical intermediate, Boc-L-Glutamic acid 5-benzylester plays a crucial role in the production of drugs that target specific medical conditions. Its versatility in chemical reactions and compatibility with other compounds make it an essential component in the pharmaceutical industry's drug development process.

InChI:InChI=1/C17H23NO6/c1-17(2,3)24-16(22)18-13(15(20)21)9-10-14(19)23-11-12-7-5-4-6-8-12/h4-8,13H,9-11H2,1-3H3,(H,18,22)(H,20,21)/p-1/t13-/m0/s1

Upstream product

• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 1676-73-9 L-glutamic acid γ-benzyl ester 
• 18595-34-1 tert-butyl fluoroformate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 13574-84-0 dicyclohexylamine salt of γ-benzyl Boc-glutamate 
• 51814-47-2 N-Boc-L-glutamic acid (γ-benzyl) α-phenacyl ester 
• 16965-08-5 1,1-dimethylethyl 2,4,5-trichlorophenyl carbonate 
• 617-65-2 Glutamic acid 
• 104-15-4 toluene-4-sulfonic acid 
• 100-51-6 benzyl alcohol 
• 132090-12-1 Boc-Glu(OBn)-OCH₂CHCH₂ 
• 100-39-0 benzyl bromide 
• 56-86-0 L-glutamic acid 

Downstream Products

• 7536-59-6 Boc-Glu(OBzl)-ONp 
• 59279-58-2 N^α-tert-butyloxycarbonyl-γ-benzyloxycarbonyl-L-glutamic acid methyl ester 
• 79722-13-7 N-Boc-γ-Bzl-L-Glu-NHOBzl 
• 117997-74-7 (S)-4-tert-Butoxycarbonylamino-4-dipropylcarbamoyl-butyric acid benzyl ester 
• 53935-21-0 tert-Butoxycarbonyl-L-glutamyl(ω-benzylester)-L-alanin-benzylester 
• 38517-49-6 Boc-Glu(Bzl)-D-Glu(Bzl)-OMte 
• 189941-34-2 (2S,3R)-3-Benzyloxy-2-((S)-4-benzyloxycarbonyl-2-tert-butoxycarbonylamino-butyrylamino)-butyric acid methyl ester 
• 203940-79-8 (S)-2-tert-Butoxycarbonylamino-pentanedioic acid 5-benzyl ester 1-[2-(toluene-4-sulfonyl)-ethyl] ester 
• 73984-05-1 H-L-Lys-Gly-L-Asp-L-Glu-L-Glu-L-Ser-L-Leu-L-Ala-OH 
• 185817-70-3 N-Boc-L-Glu(OBn)-O-nHex 
• 341969-33-3 Boc-Glu(OBzl)-Pro-Aib-Pro-Tyr-OBzl 

Relevant articles and documents

RETRACTED ARTICLE: Asymmetric Synthesis of Apratoxin e

An efficient method for asymmetric synthesis of apratoxin E 2 is described in this report. The chiral lactone 8, recycled from the degradation of saponin glycosides, was utilized to prepare the non-peptide fragment 6. In addition to this "from nature to nature" strategy, olefin cross-metathesis (CM) was applied as an alternative approach for the formation of the double bond. Moreover, pentafluorophenyl diphenylphosphinate was found to be an efficient condensation reagent for the macrocyclization.

SPIRO-LACTAM NMDA RECEPTOR MODULATORS AND USES THEREOF

Disclosed are compounds having potency in the modulation of NMDA receptor activity. Such compounds can be used in the treatment of conditions such as depression and related disorders as well as other disorders.

Rhamnolipid inspired lipopeptides effective in preventing adhesion and biofilm formation of Candida albicans

Rhamnolipids are biodegradable low toxic biosurfactants which exert antimicrobial and anti-biofilm properties. They have attracted much attention recently due to potential applications in areas of bioremediation, therapeutics, cosmetics and agriculture, however, the full potential of these versatile molecules is yet to be explored. Based on the facts that many naturally occurring lipopeptides are potent antimicrobials, our study aimed to explore the potential of replacing rhamnose in rhamnolipids with amino acids thus creating lipopeptides that would mimic or enhance properties of the parent molecule. This would allow not only for more economical and greener production but also, due to the availability of structurally different amino acids, facile manipulation of physico-chemical and biological properties. Our synthetic efforts produced a library of 43 lipopeptides revealing biologically more potent molecules. The structural changes significantly increased, in particular, anti-biofilm properties against Candida albicans, although surface activity of the parent molecule was almost completely abolished. Our findings show that the most active compounds are leucine derivatives of 3-hydroxy acids containing benzylic ester functionality. The SAR study demonstrated a further increase in activity with aliphatic chain elongation. The most promising lipopeptides 15, 23 and 36 at 12.5 μg/mL concentration allowed only 14.3%, 5.1% and 11.2% of biofilm formation, respectively after 24 h. These compounds inhibit biofilm formation by preventing adhesion of C. albicans to abiotic and biotic surfaces.

Controlled ring-opening polymerization of α-amino acid N-carboxy-anhydride by frustrated amine/borane Lewis pairs

In this communication, we presented a novel strategy to control the ROP of α-amino acid N-carboxy-anhydrides using the concept of frustrated Lewis pairs (FLPs). An FLP intermediate containing an interaction between the bulky borane Lewis acid and the amine groups of the propagation chain end is essential to accomplish the polypeptide synthesis with well-defined structures under mild conditions.

Desyl and phenacyl as versatile, photocatalytically cleavable protecting groups: A classic approach in a different (visible) light

A highly efficient, catalytic strategy for the deprotection of classical phenacyl (Pac) as well as desyl (Dsy) protection groups has been developed using visible light photoredox catalysis. The deliberate use of a neutral two-phase acetonitrile/water mixture with K3PO4 applying catalytic amounts of [Ru(bpy)3](PF6)2 in combination with ascorbic acid is the key to this truly catalytic deprotection of Pac- and Dsy-protected carboxylic acids. Our mild yet robust protocol allows for fast and selective liberation of the free carboxylic acids in very good to quantitative yields, while only low catalyst loadings (1 mol %) are required. Both Pac and Dsy, easily introduced from commercially available precursors, can be applied for the direct protection of carboxylic acids and amino acids, offering orthogonality to a great variety of other common protecting groups. We further demonstrate the general applicability and versatility of these formerly underrated protecting groups in combination with our catalytic cleavage conditions, as underscored by the gained high functional group tolerance. Moreover, this method could successfully be adapted to the requirements of solidphase synthesis. As a proof of principle for an efficient visible light, photocatalytic linker cleavage, a Boc-protected tripeptide was split off from commercially available brominated Wang resin.

DRUG DERIVATIVES

The present invention relates to derivatives of known active pharmaceutical compounds. These derivatives are differentiated from the parent active compound by virtue of being redox derivatives of the active compound. This means that one or more of the functional groups in the active compound has been converted to another group in one or more reactions which may be considered to represent a change of oxidation state. We refer to these compounds generally as redox derivatives. The derivatives of the invention may be related to the original parent active pharmaceutical compound by only a single step transformation, or may be related via several synthetic steps including one or more changes of oxidation state. In certain cases, the functional group obtained after two or more transformations may be in the same oxidation state as the parent active compound (and we include these compounds in our definition of redox derivatives). In other cases, the oxidation state of the derivative of the invention may be regarded as being different from that of the parent compound. In many cases, the compounds of the invention have inherent therapeutic activity on their own account. In some cases, this activity relative to the same target or targets of the parent compound is as good as or better than the activity which the parent compound has against the target or targets.

DRUG DERIVATIVES

The present invention relates to derivatives of known active pharmaceutical compounds. These derivatives are differentiated from the parent active compound by virtue of being redox derivatives of the active compound. This means that one or more of the functional groups in the active compound has been converted to another group in one or more reactions which may be considered to represent a change of oxidation state. We refer to these compounds generally as redox derivatives. The derivatives of the invention may be related to the original parent active pharmaceutical compound by only a single step transformation, or may be related via several synthetic steps including one or more changes of oxidation state. In certain cases, the functional group obtained after two or more transformations may be in the same oxidation state as the parent active compound (and we include these compounds in our definition of redox derivatives). In other cases, the oxidation state of the derivative of the invention may be regarded as being different from that of the parent compound. In many cases, the compounds of the invention have inherent therapeutic activity on their own account. In some cases, this activity relative to the same target or targets of the parent compound is as good as or better than the activity which the parent compound has against the target or targets.

Synthesis and biological evaluation of boron peptide analogues of Belactosin C as proteasome inhibitors

A series of boron peptides 11, 13, 15 and 17 were designed and synthesized as proteasome inhibitors based on the structure of Belactosin C. Matteson homologation was a key step in the synthesis of the boron peptides. Compounds 11a and 13 showed significant inhibition of 20S proteasome chymotrypsin-like (β5) activity (IC50 = 0.28 and 0.51 μM, respectively). Furthermore, like PS-341, compound 11a increased the G2/M cell distribution. A biparametric cytofluorimetric analysis with FITC-labeled annexin V and propidium iodide showed induction of apoptosis by compound 11a at >1 μM concentrations of compound.

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.

NOVEL INTEGRIN BINDING RGD-LIPOPEPTIDES WITH GENE TRANSFER ACTIVITIES

The present invention provides synthesis of a novel series of cationic lipopeptides with integrin-binding RGD functionalities. The invention also provides phenomenally high L27 (transformed Sl 80, mouse sarcoma cells) cell tropic gene transfer properties of these novel RGD-lipopeptides. Since L27 cell surface contains over expressed integrins, the present class of lipopeptides with integrin-binding RGD ligands are likely to find future applications in targeting anti-cancer genes/drugs to the endothelial cells of tumor vasculatures (possessing over expressed integrins).