Boc-D-aspartic acid β-9-fluorenylmethyl ester
Need Assistance?
  • US & Canada:
    +
  • UK: +

Boc-D-aspartic acid β-9-fluorenylmethyl 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-002707
CAS number
123417-19-6
Molecular Formula
C23H25NO6
Molecular Weight
411.50
Boc-D-aspartic acid β-9-fluorenylmethyl ester
IUPAC Name
(2R)-4-(9H-fluoren-9-ylmethoxy)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoic acid
Synonyms
Boc-D-Asp(OFm)-OH; (R)-4-((9H-Fluoren-9-yl)methoxy)-2-((tert-butoxycarbonyl)amino)-4-oxobutanoic acid
Appearance
White powder
Purity
≥ 99% (HPLC)
Melting Point
139-141 °C
Storage
Store at 2-8°C
InChI
InChI=1S/C23H25NO6/c1-23(2,3)30-22(28)24-19(21(26)27)12-20(25)29-13-18-16-10-6-4-8-14(16)15-9-5-7-11-17(15)18/h4-11,18-19H,12-13H2,1-3H3,(H,24,28)(H,26,27)/t19-/m1/s1
InChI Key
NHLRMCFWGFPSLT-LJQANCHMSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13)C(=O)O

Boc-D-aspartic acid β-9-fluorenylmethyl ester, a specialized chemical compound utilized widely in peptide synthesis, boasts diverse applications. Below are four key applications presented with elevated perplexity and burstiness:

Peptide Synthesis: Playing a pivotal role in solid-phase peptide synthesis, Boc-D-aspartic acid β-9-fluorenylmethyl ester serves as a protected amino acid derivative. The Boc (tert-butyloxycarbonyl) group shields the amine function during coupling reactions, allowing for selective deprotection as needed. This enables the meticulous assembly of peptides with exceptional precision and purity, elevating the standards of peptide synthesis.

Drug Development: In the pharmaceutical sector, Boc-D-aspartic acid β-9-fluorenylmethyl ester stands as a cornerstone for crafting peptide-based drugs and conjugates. Researchers leverage this compound to synthesize peptides with specific sequences, primed for evaluation of therapeutic efficacy. This application plays a pivotal role in the innovation of novel treatments for afflictions like cancer, metabolic disorders, and infectious diseases, reshaping the landscape of drug development.

Protein Engineering: Facilitating the creation of tailor-made peptides for protein engineering and functional analyses, Boc-D-aspartic acid β-9-fluorenylmethyl ester is a game-changer. By integrating these synthetic peptides into larger protein frameworks, scientists can probe protein interactions, stability, and activity. This approach aids in the design of proteins endowed with enhanced properties, ideal for applications in biotechnology and therapeutics, propelling the field of protein engineering to new heights.

Biochemical Research: In the realm of biochemical investigations, this compound plays an indispensable role, particularly in elucidating enzyme-substrate interactions and protein-ligand binding dynamics. By incorporating Boc-D-aspartic acid β-9-fluorenylmethyl ester into experimental setups, researchers can dissect the impacts of specific amino acid modifications. This contributes significantly to unraveling intricate biochemical pathways and molecular mechanisms, enriching our comprehension of the molecular world.

1. Boronate-Based Fluorescent Probes as a Prominent Tool for H2O2 Sensing and Recognition
Ling Wang, Xuben Hou, Hao Fang, Xinying Yang Curr Med Chem. 2022;29(14):2476-2489. doi: 10.2174/0929867328666210902101642.
Given the crucial association of hydrogen peroxide with a wide range of human diseases, this compound has currently earned the reputation of being a popular biomolecular target. Although various analytical methods have attracted our attention, fluorescent probes have been used as prominent tools to determine H2O2 to reflect the physiological and pathological conditions of biological systems. The sensitive responsive part of these probes is the boronate ester and boronic acid groups, which are important reporters for H2O2 recognition. In this review, we summarize boronate ester/boronic acid group-based fluorescent probes for H2O2 reported from 2012 to 2020, and we have generally classified the fluorophores into six categories to exhaustively elaborate the design strategy and comprehensive systematic performance. We hope that this review will inspire the exploration of new fluorescent probes based on boronate ester/boronic acid groups for the detection of H2O2 and other relevant analytes.
2. Photocatalytic direct borylation of carboxylic acids
Qiang Wei, Yuhsuan Lee, Weiqiu Liang, Xiaolei Chen, Bo-Shuai Mu, Xi-Yang Cui, Wangsuo Wu, Shuming Bai, Zhibo Liu Nat Commun. 2022 Nov 19;13(1):7112. doi: 10.1038/s41467-022-34833-1.
The preparation of high value-added boronic acids from cheap and plentiful carboxylic acids is desirable. To date, the decarboxylative borylation of carboxylic acids is generally realized through the extra step synthesized redox-active ester intermediate or in situ generated carboxylic acid covalent derivatives above 150 °C reaction temperature. Here, we report a direct decarboxylative borylation method of carboxylic acids enabled by visible-light catalysis and that does not require any extra stoichiometric additives or synthesis steps. This operationally simple process produces CO2 and proceeds under mild reaction conditions, in terms of high step economy and good functional group compatibility. A guanidine-based biomimetic active decarboxylative mechanism is proposed and rationalized by mechanistic studies. The methodology reported herein should see broad application extending beyond borylation.
3. Tris(pentafluorophenyl)borane-Catalyzed Reactions Using Silanes
Taylor Hackel, Nicholas A McGrath Molecules. 2019 Jan 25;24(3):432. doi: 10.3390/molecules24030432.
The utility of an electron-deficient, air stable, and commercially available Lewis acid tris(pentafluorophenyl)borane has recently been comprehensively explored. While being as reactive as its distant cousin boron trichloride, it has been shown to be much more stable and capable of catalyzing a variety of powerful transformations, even in the presence of water. The focus of this review will be to highlight those catalytic reactions that utilize a silane as a stoichiometric reductant in conjunction with tris(pentafluorophenyl) borane in the reduction of alcohols, carbonyls, or carbonyl-like derivatives.
Online Inquiry
Verification code
Inquiry Basket