Boc-L-aspartic acid β-tert-butyl ester
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Boc-L-aspartic acid β-tert-butyl ester

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Category
BOC-Amino Acids
Catalog number
BAT-002760
CAS number
1676-90-0
Molecular Formula
C13H23NO6
Molecular Weight
289.40
Boc-L-aspartic acid β-tert-butyl ester
IUPAC Name
(2S)-4-[(2-methylpropan-2-yl)oxy]-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoic acid
Synonyms
Boc-L-Asp(OtBu)-OH; (S)-4-(tert-Butoxy)-2-((tert-butoxycarbonyl)amino)-4-oxobutanoic acid; N-Alpha-t-Boc-L-aspartic acid beta-t-butyl ester
Appearance
White powder
Purity
≥ 99.5% (Chiral HPLC)
Density
1.139±0.06 g/cm3(Predicted)
Melting Point
50-65 °C
Boiling Point
432.6±40.0 °C(Predicted)
Storage
Store at 2-8 °C
InChI
InChI=1S/C13H23NO6/c1-12(2,3)19-9(15)7-8(10(16)17)14-11(18)20-13(4,5)6/h8H,7H2,1-6H3,(H,14,18)(H,16,17)/t8-/m0/s1
InChI Key
PHJDCONJXLIIPW-QMMMGPOBSA-N
Canonical SMILES
CC(C)(C)OC(=O)CC(C(=O)O)NC(=O)OC(C)(C)C

Boc-L-aspartic acid β-tert-butyl ester, a protective derivative of aspartic acid, commonly utilized in peptide synthesis, serves versatile purposes in various applications. Here are four key applications presented with heightened perplexity and burstiness:

Peptide Synthesis: Integral to solid-phase peptide synthesis (SPPS), Boc-L-aspartic acid β-tert-butyl ester plays a pivotal role in safeguarding the α-amino group and the β-carboxyl group of aspartic acid. This protective function allows for the systematic addition of amino acids to construct peptides devoid of undesired side reactions. Its utilization guarantees the precise and effective assembly of peptide chains, indispensable for both research endeavors and therapeutic advancements.

Bioconjugation Studies: Within the realm of bioconjugation techniques, this compound proves invaluable for linking peptides or proteins to other biomolecules or synthetic counterparts. The incorporation of the protected aspartic acid derivative into peptides enables site-specific modifications post-deprotection. Such modifications are critical for the development of targeted drug delivery systems and diagnostic instruments, enhancing precision and efficacy in biomedical applications.

Protein Engineering: In the domain of protein engineering, Boc-L-aspartic acid β-tert-butyl ester facilitates the strategic introduction of aspartic acid residues at specific loci within proteins. This strategic placement aids in elucidating the intricate relationships between protein structure and function, enabling the design of proteins with augmented or novel characteristics. Researchers can selectively tailor protein sequences to deepen their understanding of folding dynamics, stability, and catalytic activities, driving forward advancements in biotechnology.

Pharmaceutical Development: Within the pharmaceutical sector, this compound serves as a cornerstone in the synthesis of peptide-based drugs and therapeutic agents. Its role in shielding reactive groups during synthesis ensures the production of high-purity products, crucial for the potency and safety of pharmaceutical formulations. This meticulous protection process is particularly paramount in the creation of peptide vaccines, enzyme inhibitors, and hormone mimetics, underpinning the development of cutting-edge pharmaceutical solutions.

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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