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Application Area

Fmoc-D-aspartic acid α-tert-butyl ester

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Category

Fmoc-Amino Acids

Catalog number

BAT-004564

CAS number

134098-70-7

Molecular Formula

C23H25NO6

Molecular Weight

411.50

IUPAC Name

(3R)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-[(2-methylpropan-2-yl)oxy]-4-oxobutanoic acid

Synonyms

Fmoc-D-Asp-OtBu

Appearance

White powder

Purity

≥ 99% (HPLC)

Density

1.251±0.06 g/cm3(Predicted)

Melting Point

103-109 °C

Boiling Point

617.4±55.0 °C(Predicted)

Storage

Store at 2-8 °C

InChI

InChI=1S/C23H25NO6/c1-23(2,3)30-21(27)19(12-20(25)26)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,25,26)/t19-/m1/s1

InChI Key

VZXQYACYLGRQJU-LJQANCHMSA-N

Canonical SMILES

CC(C)(C)OC(=O)C(CC(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13

Fmoc-D-aspartic acid α-tert-butyl ester plays a pivotal role in peptide synthesis and a range of biological applications. Here are four key applications:

Peptide Synthesis: The versatile Fmoc-D-aspartic acid α-tert-butyl ester is a cornerstone in the solid-phase synthesis of peptides. The strategic use of the Fmoc (Fluorenylmethyloxycarbonyl) group shields the amino terminus, safeguarding against undesired reactions during peptide elongation. Meanwhile, the tert-butyl ester provides precise protection for the carboxyl group, ensuring flawless chain assembly.

Pharmaceutical Research: In the realm of drug discovery, Fmoc-D-aspartic acid α-tert-butyl ester emerges as a crucial component in the design and synthesis of peptide-based drugs. The protective groups simplify the integration of D-aspartic acid into peptide sequences, enabling researchers to explore the therapeutic efficacy and bioactivity of peptide analogs in combating various diseases.

Structural Biology: Delving into protein-protein interactions and protein structure analysis, this compound facilitates the synthesis of peptides incorporating Fmoc-D-aspartic acid α-tert-butyl ester. Through these peptides, researchers unravel how specific amino acid modifications influence protein folding and function, shedding light on protein stability, binding affinities, and conformational dynamics.

Biomaterial Development: A key player in biomaterial innovation, Fmoc-D-aspartic acid α-tert-butyl ester contributes to the creation of cutting-edge biomaterials, particularly peptide-based hydrogels and scaffolds. By leveraging the ester and Fmoc groups, researchers can meticulously control polymerization and cross-linking, fine-tuning the mechanical properties and bioactivity of the resulting biomaterials.

1.Preparation of vitamin B6-conjugated peptides at the amino terminus and of vitamin B6-peptide-oligonucleotide conjugates.

Zhu T1, Stein S. Bioconjug Chem. 1994 Jul-Aug;5(4):312-5.

A series of N-(4'-pyridoxyl)peptides has been made by standard Fmoc chemistry and a solid-phase coupling procedure. The last Fmoc group of the peptide was removed on the synthesizer, and the free amino group was then condensed with pyridoxal. The Schiff base formed was selectively reduced using sodium cyanoborohydride. The product was cleaved from the resin using a standard procedure. No deleterious effects were found when using the protected amino acids Fmoc-L-Ala, Fmoc-L-Arg(Pmc), Fmoc-L-Asp(OtBu), Fmoc-L-His(Trt), Fmoc-L-Ser(tBu), Fmoc-L-Thr(tBu), and Fmoc-L-Cys(Trt) for peptide synthesis. A vitamin B6-peptide-oligonucleotide conjugate could be synthesized using a cysteinyl peptide and a suitably activated oligonucleotide.

2.Synthesis of various 3-substituted 1,2,4-oxadiazole-containing chiral beta 3- and alpha-amino acids from Fmoc-protected aspartic acid.

Hamzé A1, Hernandez JF, Fulcrand P, Martinez J. J Org Chem. 2003 Sep 19;68(19):7316-21.

Various 3-substituted chiral 1,2,4-oxadiazole-containing Fmoc-beta(3)- and -alpha-amino acids were synthesized from Fmoc-(l or d)-Asp(OtBu)-OH and Fmoc-l-Asp-OtBu, respectively, in three steps (i.e., condensation of an aspartyl derivative with differentially substituted amidoximes, formation of the 1,2,4-oxadiazole, and cleavage of the tert-butyl ester). These compounds represent new series of nonnatural amino acids, which could be used in combinatorial synthesis. A simple protocol has been developed to generate the 1,2,4-oxadiazole ring. Indeed, common methods resulted in cleavage of the Fmoc group or required long reaction times. We found that sodium acetate in refluxing ethanol/water (86 degrees C) was a convenient and efficient catalyst to promote conversion of Fmoc-amino acyl amidoximes to 1,2,4-oxadiazoles, and this procedure proved to be compatible with Fmoc protection. It is shown that these compounds can be prepared without significant loss of enantiomerical purity.

3.Solid-Phase Total Synthesis of Bacitracin A.

Lee J1, Griffin JH, Nicas TI. J Org Chem. 1996 Jun 14;61(12):3983-3986.

An efficient solid-phase method for the total synthesis of bacitracin A is reported. This work was undertaken in order to provide a general means of probing the intriguing mode of action of the bacitracins and exploring their potential for use against emerging drug-resistant pathogens. The synthetic approach to bacitracin A involves three key features: (1) linkage to the solid support through the side chain of the L-asparaginyl residue at position 12 (L-Asn(12)), (2) cyclization through amide bond formation between the alpha-carboxyl of L-Asn(12) and the side chain amino group of L-Lys(8), and (3) postcyclization addition of the N-terminal thiazoline dipeptide as a single unit. To initiate the synthesis, Fmoc L-Asp(OH)-OAllyl was attached to a PAL resin. The chain of bacitracin A was elaborated in the C-to-N direction by sequential piperidine deprotection/HBTU-mediated coupling cycles with Fmoc D-Asp(OtBu)-OH, Fmoc L-His(Trt)-OH, Fmoc D-Phe-OH, Fmoc L-Ile-OH, Fmoc D-Orn(Boc)-OH, Fmoc L-Lys(Aloc)-OH, Fmoc L-Ile-OH, Fmoc D-Glu(OtBu)-OH, and Fmoc L-Leu-OH.