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Application Area

Boc-N-methyl-L-glutamic acid γ-benzyl ester

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Category

BOC-Amino Acids

Catalog number

BAT-002832

CAS number

200615-91-4

Molecular Formula

C18H25NO6

Molecular Weight

351.4

Boc-N-methyl-L-glutamic acid γ-benzyl ester

IUPAC Name

(2S)-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]-5-oxo-5-phenylmethoxypentanoic acid

Synonyms

Boc-N-Me-L-Glu(OBzl)-OH; Boc-N-methyl-L-glutamic acid 5-benzyl ester

Appearance

White to off-white powder

Purity

≥ 95% (NMR)

Density

1.184 g/cm3

Storage

Store at 2-8 °C

InChI

InChI=1S/C18H25NO6/c1-18(2,3)25-17(23)19(4)14(16(21)22)10-11-15(20)24-12-13-8-6-5-7-9-13/h5-9,14H,10-12H2,1-4H3,(H,21,22)/t14-/m0/s1

InChI Key

NEJPFSNBCOTZHN-AWEZNQCLSA-N

Canonical SMILES

CC(C)(C)OC(=O)N(C)C(CCC(=O)OCC1=CC=CC=C1)C(=O)O

Boc-N-methyl-L-glutamic acid γ-benzyl ester, a versatile chemical compound utilized in both organic synthesis and pharmaceutical research, finds diverse applications in scientific endeavors. Here are four key applications:

Peptide Synthesis: Serving as a crucial protective group in the realm of peptide synthesis, Boc-N-methyl-L-glutamic acid γ-benzyl ester enables the selective deprotection of amine functionalities while preserving the integrity of carboxylic groups. This compound facilitates the construction of intricate peptides featuring multiple reactive sites. Its employment guarantees the production of high-purity peptides essential for pharmaceutical advancements.

Drug Development: Moving the needle in pharmaceutical research, Boc-N-methyl-L-glutamic acid γ-benzyl ester plays a pivotal role as an intermediate for synthesizing novel therapeutic compounds. By incorporating this ester into synthesizable frameworks, researchers can explore its potential to enhance the bioavailability and stability of drug candidates. Its adaptability in chemical modifications positions it as a valuable asset in developing compounds boasting favorable pharmacokinetic profiles.

Chirality Studies: In the realm of chirality studies, Boc-N-methyl-L-glutamic acid γ-benzyl ester shines bright due to its capability to introduce chiral centers into synthetic compounds. This aspect proves instrumental in the exploration of enantiomerically pure compounds known for their heightened efficacy and safety as pharmaceutical agents. Understanding chirality and its impact on biological activity stands as a cornerstone for designing drugs tailored to interact precisely with biological targets.

Organic Synthesis: As an ester derivative, Boc-N-methyl-L-glutamic acid γ-benzyl ester takes center stage in various organic synthesis reactions aimed at constructing intricate molecular architectures. Its utility in multi-step synthesis pathways empowers chemists to craft sophisticated molecules adorned with multiple functional groups. This application plays a pivotal role in advancing synthetic chemistry research and fostering the creation of novel materials and chemical tools.

1. Nano Aggregate Formation Through Self-Assembly of Poly(L-lysine)-Block-Poly( γ-benzyl-L-glutamate)-Graft-Poly(ethylene glycol) Copolymer

Yu Zhang, Wenliang Song, Il Kim J Nanosci Nanotechnol. 2020 Nov 1;20(11):6968-6974. doi: 10.1166/jnn.2020.18818.

Polymeric nano aggregates based on poly(L-lysine)-block-PBLG-graft-poly(ethylene glycol) (PLL-b-PBLG-g-PEG) copolymers were prepared by a dialysis method in deionized water. PLL-b-PBLG-g-PEG copolymers with different degrees of PEG substitution were synthesized by combining the ring-opening polymerization of α-amino acid N-carboxyanhydrides and ester exchange reactions. Proton nuclear magnetic resonance spectroscopy and gel permeation chromatography were employed to confirm the polymer structures and molecular weights. Transmission electron microscopy and dynamic light scattering were used to observe the self-assembly behavior. The experimental results revealed that the volume content of deionized water in the mixture significantly affects the morphology and size of the aggregates formed by PLL-b-PBLG-g-PEG copolymers. Spherical, spindle-like, needle-like, and daisy-like aggregates were observed with an increase in the volume content of deionized water in the mixture.

2. Aminated Graphene-Graft-Oligo(Glutamic Acid) /Poly(ε-Caprolactone) Composites: Preparation, Characterization and Biological Evaluation

Mariia Stepanova, et al. Polymers (Basel). 2021 Aug 7;13(16):2628. doi: 10.3390/polym13162628.

Biodegradable and biocompatible composites are of great interest as biomedical materials for various regeneration processes such as the regeneration of bones, cartilage and soft tissues. Modification of the filler surface can improve its compatibility with the polymer matrix, and, as a result, the characteristics and properties of composite materials. This work is devoted to the synthesis and modification of aminated graphene with oligomers of glutamic acid and their use for the preparation of composite materials based on poly(ε-caprolactone). Ring-opening polymerization of N-carboxyanhydride of glutamic acid γ-benzyl ester was used to graft oligomers of glutamic acid from the surface of aminated graphene. The success of the modification was confirmed by Fourier-transform infrared and X-ray photoelectron spectroscopy as well as thermogravimetric analysis. In addition, the dispersions of neat and modified aminated graphene were analyzed by dynamic and electrophoretic light scattering to monitor changes in the characteristics due to modification. The poly(ε-caprolactone) films filled with neat and modified aminated graphene were manufactured and carefully characterized for their mechanical and biological properties. Grafting of glutamic acid oligomers from the surface of aminated graphene improved the distribution of the filler in the polymer matrix that, in turn, positively affected the mechanical properties of composite materials in comparison to ones containing the unmodified filler. Moreover, the modification improved the biocompatibility of the filler with human MG-63 osteoblast-like cells.

3. Therapeutic melanoma inhibition by local micelle-mediated cyclic nucleotide repression

Kerstin Johann, et al. Nat Commun. 2021 Oct 13;12(1):5981. doi: 10.1038/s41467-021-26269-w.

The acidic tumor microenvironment in melanoma drives immune evasion by up-regulating cyclic adenosine monophosphate (cAMP) in tumor-infiltrating monocytes. Here we show that the release of non-toxic concentrations of an adenylate cyclase (AC) inhibitor from poly(sarcosine)-block-poly(L-glutamic acid γ-benzyl ester) (polypept(o)id) copolymer micelles restores antitumor immunity. In combination with selective, non-therapeutic regulatory T cell depletion, AC inhibitor micelles achieve a complete remission of established B16-F10-OVA tumors. Single-cell sequencing of melanoma-infiltrating immune cells shows that AC inhibitor micelles reduce the number of anti-inflammatory myeloid cells and checkpoint receptor expression on T cells. AC inhibitor micelles thus represent an immunotherapeutic measure to counteract melanoma immune escape.