Fmoc-L-aspartic acid β-tert-butyl ester α-N-hydroxysuccinimide ester
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Fmoc-L-aspartic acid β-tert-butyl ester α-N-hydroxysuccinimide ester

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Category
Fmoc-Amino Acids
Catalog number
BAT-003746
CAS number
78553-23-8
Molecular Formula
C27H28N2O8
Molecular Weight
508.50
Fmoc-L-aspartic acid β-tert-butyl ester α-N-hydroxysuccinimide ester
IUPAC Name
4-O-tert-butyl 1-O-(2,5-dioxopyrrolidin-1-yl) (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)butanedioate
Synonyms
Fmoc-L-Asp(OtBu)-OSu; (S)-4-tert-Butyl 1-(2,5-dioxopyrrolidin-1-yl) 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)succinate; Fmoc-L-aspartic acid 4-tert-butyl 1-(hydroxysuccinimide) ester
Appearance
White powder
Purity
≥ 98% (HPLC)
Storage
Store at 2-8 °C
InChI
InChI=1S/C27H28N2O8/c1-27(2,3)36-24(32)14-21(25(33)37-29-22(30)12-13-23(29)31)28-26(34)35-15-20-18-10-6-4-8-16(18)17-9-5-7-11-19(17)20/h4-11,20-21H,12-15H2,1-3H3,(H,28,34)/t21-/m0/s1
InChI Key
OCCFRTKCROFJLW-NRFANRHFSA-N
Canonical SMILES
CC(C)(C)OC(=O)CC(C(=O)ON1C(=O)CCC1=O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24

Fmoc-L-aspartic acid β-tert-butyl ester α-N-hydroxysuccinimide ester plays a pivotal role in peptide synthesis and bioconjugation. Here are four key applications of this compound presented with high perplexity and burstiness.

Peptide Synthesis: This specialized reagent features prominently in solid-phase peptide synthesis (SPPS), a technique utilized to craft custom peptides of exceptional purity. By safeguarding the N-terminal end and side chain of aspartic acid, it ensures precise deprotection during the elongation process, thereby streamlining the production of intricate peptides tailored for diverse research and pharmaceutical endeavors.

Protein Labeling: With its ester functional group, this compound serves as a potent crosslinker in protein labeling applications. By engaging with amine groups on proteins, it proficiently conjugates fluorophores, biotin, or other labels to proteins, facilitating pivotal techniques like fluorescence microscopy, Western blotting, and flow cytometry, thus broadening the horizons of protein analysis and visualization.

Bioconjugation: Embedded within bioconjugation strategies, Fmoc-L-aspartic acid β-tert-butyl ester α-N-hydroxysuccinimide ester acts as a linchpin in linking peptides with a myriad of biomolecules. Whether conjugated to antibodies, enzymes, or nucleic acids, this compound enhances the functionality and detectability of these bioconjugates, playing an indispensable role in the creation of diagnostic assays and therapeutic agents that push the boundaries of medical innovation.

Drug Delivery Systems: In the domain of drug delivery systems, this compound emerges as a crucial component in facilitating the targeted delivery of therapeutic agents. By enabling the attachment of peptides to drug carriers such as nanoparticles or liposomes, it propels the precise delivery of therapeutic payloads to designated sites, enhancing treatment efficacy while mitigating adverse side effects.

1. Asymmetric synthesis of trans-2,3-piperidinedicarboxylic acid and trans-3,4-piperidinedicarboxylic acid derivatives
Chu-Biao Xue, Xiaohua He, John Roderick, Ronald L Corbett, Carl P Decicco J Org Chem. 2002 Feb 8;67(3):865-70. doi: 10.1021/jo016086b.
Asymmetric syntheses of (2S,3S)-3-(tert-butoxycarbonyl)-2-piperidinecarboxylic acid (1b), (3R,4S)-4-(tert-butoxycarbonyl)-3-piperidinecarboxylic acid (2b), and their corresponding N-Boc and N-Cbz protected analogues 8a,b and 17a,b are described. Enantiomerically pure 1b has been synthesized in five steps starting from L-aspartic acid beta-tert-butyl ester. Tribenzylation of the starting material followed by alkylation with allyl iodide using KHMDS produces the key intermediate 5a in a 6:1 diastereomeric excess. Upon hydroboration, the alcohol 6a is oxidized, and the resulting aldehyde 7 is subjected to a ring closure via reductive amination, providing 1b in an overall yield of 38%. Optically pure 2b has been synthesized beginning with N-Cbz-beta-alanine. The synthesis involves the induction of the first stereogenic center using Evans's chemistry and sequential LDA-promoted alkylations with tert-butyl bromoacetate and allyl iodide. Further elaboration by ozonolysis and reductive amination affords 2b in an overall yield of 28%.
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