N-α-(t-Butoxycarbonyl)-L-glutamic acid γ-benzyl ester α-methyl ester
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N-α-(t-Butoxycarbonyl)-L-glutamic acid γ-benzyl ester α-methyl ester

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Category
BOC-Amino Acids
Catalog number
BAT-003126
CAS number
59279-58-2
Molecular Formula
C18H25NO6
Molecular Weight
351.39
N-α-(t-Butoxycarbonyl)-L-glutamic acid γ-benzyl ester α-methyl ester
IUPAC Name
5-O-benzyl 1-O-methyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanedioate
Synonyms
Boc-Glu(OBzl)-OMe; 5-O-benzyl 1-O-methyl(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanedioate; (2S)-2-tert-butoxycarbonylaminopentanedioic acid 5-benzyl ester 1-methyl ester; (S)-2-tert-Butoxycarbonylamino-pentanedioic acid 5-benzyl ester 1-methyl ester; Boc-L-Glu(OBn)-OMe
Appearance
White solid
Purity
≥ 95%
Storage
Store at 2-8 °C
InChI
InChI=1S/C18H25NO6/c1-18(2,3)25-17(22)19-14(16(21)23-4)10-11-15(20)24-12-13-8-6-5-7-9-13/h5-9,14H,10-12H2,1-4H3,(H,19,22)/t14-/m0/s1
InChI Key
KHCZTGSAKNZBOV-AWEZNQCLSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CCC(=O)OCC1=CC=CC=C1)C(=O)OC

N-α-(t-Butoxycarbonyl)-L-glutamic acid γ-benzyl ester α-methyl ester is a versatile amino acid derivative widely utilized in peptide synthesis and biochemical research. Here are four key applications of this compound:

Peptide Synthesis: Serving as a vital foundational component in peptide synthesis, N-α-(t-Butoxycarbonyl)-L-glutamic acid γ-benzyl ester α-methyl ester plays a crucial role. The strategic incorporation of protective groups allows chemists to selectively unveil specific functional groups, facilitating the gradual extension of peptide chains in a controlled manner. This methodical approach enables the construction of intricate peptides, essential for advancing research in drug discovery and protein engineering.

Chemical Biology: Embraced in the realm of chemical biology, this compound fuels investigations into protein interactions and functions. By integrating it as a non-native amino acid into proteins, researchers gain insight into protein behavior under varying conditions. Through targeted modifications at specific protein sites, scientists can probe the contributions of individual residues to biochemical processes, unraveling the intricacies of molecular interactions.

Pharmaceutical Development: Positioned at the frontier of pharmaceutical innovation, N-α-(t-Butoxycarbonyl)-L-glutamic acid γ-benzyl ester α-methyl ester plays a pivotal role in enhancing the stability and efficacy of pharmaceutical candidates. In the realm of drug design, structural modifications using such derivatives elevate drug bioavailability and therapeutic potency. This progressive approach facilitates the creation of peptide-based therapeutics that not only exhibit heightened effectiveness but also boast reduced side effects, propelling pharmaceutical advancements.

Proteomics: Within the domain of proteomics, this compound emerges as an indispensable tool for conducting mass spectrometry analyses of proteins. By labeling proteins with isotope-labeled derivatives during synthesis, researchers can quantitatively evaluate and juxtapose protein abundances across diverse samples.

1.Side reactions in solid-phase peptide synthesis and their applications.
Hsieh KH1, Demaine MM, Gurusidaiah S. Int J Pept Protein Res. 1996 Sep;48(3):292-8.
Side reactions in peptide synthesis indicate steps needing improvement as well as opportunities for structural diversification in combinatorial design. Among the side reactions observed in this study, transesterification of Boc-Glu(OBzl) occurred in TMAH-catalyzed resin attachment, leading to Boc-DKKREE(OMe) in solid-phase synthesis of Boc-DKKREE. Acetylation of Boc-Arg(NO2)-resin occurred during resin capping with Ac2O/Et3N, leading to GPR (Ac) in GPR synthesis. His- and Lys-modification occurred during GHRPLDKKREE cleavage from resin by Pd(OAc)2-catalyzed hydrogenation in DMF. To verify these side reactions, model experiments were performed, which indicated rapid transesterification of Boc-Glu(OBzl) in methyl, isopropyl, or tert-butyl alcohol into the corresponding ester by TMAH, but studies of acetylation showed that both Boc-Arg(NO2) and Boc-Arg(Tos) were stable to Ac-Im treatment, but were modified by Ac2O/Et3N. Since transfer hydrogenation of Boc-His(Bzl) and Boc-Lys(Z) in HCOOH or ammonium formate did not generate the formylated side-products of catalytic hydrogenation, DMF and not its decomposed product, HCOOH, appeared involved in side-chain modification.
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