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

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Fmoc-L-aspartic acid β-tert-butyl ester is a Fmoc-protected L-Aspartic acid 4-tert-butyl ester. L-Aspartic acid is a non-essential amino acid that is used to biosynthesize other amino acids within the human body.

Category
Fmoc-Amino Acids
Catalog number
BAT-003745
CAS number
71989-14-5
Molecular Formula
C23H25NO6
Molecular Weight
411.50
Fmoc-L-aspartic acid β-tert-butyl ester
IUPAC Name
(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-[(2-methylpropan-2-yl)oxy]-4-oxobutanoic acid
Synonyms
Fmoc-L-Asp(OtBu)-OH; FMOC-L-Asparticacidbeta-tert-butylester; Fmoc-L-aspartic acid 4-tert-butyl ester; Fmoc-Asp(OtBu)-OH; 9-fluorenyl-methoxycarbonyl-L-Asp-tert-butyl ester
Appearance
White to off-white powder
Purity
≥ 99.7% (HPLC, Chiral purity)
Density
1.251 g/cm3
Melting Point
143-150 °C
Boiling Point
530.5 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C23H25NO6/c1-23(2,3)30-20(25)12-19(21(26)27)24-22(28)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-/m0/s1
InChI Key
FODJWPHPWBKDON-IBGZPJMESA-N
Canonical SMILES
CC(C)(C)OC(=O)CC(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13

Fmoc-L-aspartic acid β-tert-butyl ester, a prominent amino acid derivative, plays a pivotal role in peptide synthesis.

Solid-Phase Peptide Synthesis (SPPS): Widely employed in SPPS, Fmoc-L-aspartic acid β-tert-butyl ester facilitates the incremental construction of peptides. The Fmoc protective group shields the amino terminus selectively, while the β-tert-butyl ester safeguards the carboxyl side chain. This orchestrated protection scheme allows for the successive incorporation of amino acids with minimal side reactions, yielding peptides of exceptional purity.

Development of Therapeutic Peptides: In the realm of therapeutic peptide synthesis, this compound plays a foundational role in producing peptides utilized in treating diverse ailments, such as cancer, diabetes, and infectious diseases. The β-tert-butyl ester protection ensures stability throughout the synthesis process, enabling the efficient generation of functional peptides. These therapeutic peptides can mimic natural proteins or disrupt disease pathways, presenting tailored treatment approaches.

Peptidomimetics Research: Integral to peptidomimetics development, Fmoc-L-aspartic acid β-tert-butyl ester aids in crafting molecules that emulate the biological functions of peptides. By integrating this protected amino acid, researchers can engineer peptide analogs with heightened stability and enhanced bioavailability. This progress in drug discovery yields sturdier and more efficacious therapeutic candidates.

Bioconjugation Studies: Prized for its specific protective properties, Fmoc-L-aspartic acid β-tert-butyl ester proves advantageous in bioconjugation investigations, where peptides are tethered to diverse molecular entities like antibodies, nanoparticles, or fluorescent dyes. The protective groups afford meticulous and regulated conjugation processes, pivotal in the advancement of inventive diagnostics and targeted drug delivery systems.

2. 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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