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

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Category
BOC-Amino Acids
Catalog number
BAT-002762
CAS number
50715-50-9
Molecular Formula
C17H26N2O8
Molecular Weight
386.40
Boc-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-[(2-methylpropan-2-yl)oxycarbonylamino]butanedioate
Synonyms
Boc-L-Asp(OtBu)-Osu; Boc-L-aspartic acida-N-hydroxysuccinimide ester
Appearance
White to off-white powder
Purity
≥ 98% (HPLC)
Density
1.25±0.1 g/cm3(Predicted)
Melting Point
101-107 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C17H26N2O8/c1-16(2,3)25-13(22)9-10(18-15(24)26-17(4,5)6)14(23)27-19-11(20)7-8-12(19)21/h10H,7-9H2,1-6H3,(H,18,24)/t10-/m0/s1
InChI Key
PIITZDSTZQZNQH-JTQLQIEISA-N
Canonical SMILES
CC(C)(C)OC(=O)CC(C(=O)ON1C(=O)CCC1=O)NC(=O)OC(C)(C)C

Boc-L-aspartic acid β-tert-butyl ester α-N-hydroxysuccinimide ester, a prominent chemical reagent in peptide synthesis and organic chemistry, boasts a multitude of applications, demonstrated below with heightened perplexity and burstiness.

Peptide Synthesis: At the forefront of solid-phase peptide synthesis (SPPS) lies this invaluable ester, pivotal for the coupling process. It intricately shields amino acid side chains and facilitates the seamless formation of peptide bonds. The distinct protection and activation attributes of this ester play a key role in orchestrating the meticulous assembly of intricate peptide sequences.

Drug Development: Engaged in the realm of drug development, Boc-L-aspartic acid β-tert-butyl ester α-N-hydroxysuccinimide ester proves instrumental in crafting peptide-based drugs. Its prowess in modifying peptide chains empowers the generation of compounds endowed with superior pharmacokinetic properties and enhanced bioavailability. This reagent stands as a cornerstone in formulating novel therapeutic agents to combat diverse medical afflictions.

Bioconjugation: Within the domain of biochemistry, this ester finds utility in the bioconjugation of peptides to a diverse array of molecules, be it fluorescent dyes or drug carriers. By fostering the formation of stable amide bonds, it streamlines the synthesis of peptide conjugates employed in diagnostics and therapeutic delivery systems. Through this process, peptides assume enhanced versatility and functionality in the realm of biomedical exploration.

Protein Engineering: Vital for protein modification and engineering in research settings, this ester plays a pivotal role. Through the targeted attachment of peptides to proteins, researchers can engineer fusion proteins endowed with unique properties and functionalities. This feature proves invaluable for studies requiring precise protein modifications and lays the foundation for protein-based biotechnological advancements.

3. 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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