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Application Area

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

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

Category

BOC-Amino Acids

Catalog number

BAT-007633

CAS number

155542-33-9

Molecular Formula

C13H23NO6

Molecular Weight

289.30

IUPAC Name

(2R)-4-[(2-methylpropan-2-yl)oxy]-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoic acid

Synonyms

Boc-D-Asp(OtBu)-OH; BOC-D-ASP(OTBU)-OH; Boc-D-aspartic acid-b-tert-butyl ester; N-alpha-t-Butoxycarbonyl-D-aspartic acid beta-t-butyl ester; (2R)-4-[(2-methylpropan-2-yl)oxy]-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoic acid; Boc-D-Asp(OBu-tert)-OH; (R)-4-tert-butoxy-2-(tert-butoxycarbonylamino)-4-oxobutanoic acid

Appearance

White to off-white powder

Purity

≥ 99% (HPLC)

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-/m1/s1

InChI Key

PHJDCONJXLIIPW-MRVPVSSYSA-N

Canonical SMILES

CC(C)(C)OC(=O)CC(C(=O)O)NC(=O)OC(C)(C)C

Boc-D-aspartic acid-β-tert-butyl ester is a chemical compound commonly used in peptide synthesis and various research applications. Here are some key applications of Boc-D-aspartic acid-β-tert-butyl ester:

Peptide Synthesis: Boc-D-aspartic acid-β-tert-butyl ester is widely used as a building block in the synthesis of peptides. It provides a protective group that is stable under certain conditions and can be removed when needed. This compound is particularly valuable in solid-phase peptide synthesis, facilitating the accurate assembly of complex peptide chains.

Pharmaceutical Development: In pharmaceutical research, Boc-D-aspartic acid-β-tert-butyl ester is utilized to create peptide-based drug candidates. Its stability and ease of incorporation into peptide chains make it an essential reagent for the development of novel therapeutics. Researchers use it to modify peptides to enhance their stability, bioavailability, and therapeutic potential.

Biochemical Research: This compound is employed in biochemical studies to investigate protein interactions and functions. By incorporating Boc-D-aspartic acid-β-tert-butyl ester into peptides, scientists can introduce specific modifications and study their effects on protein binding and activity. This application is crucial for understanding protein function and designing inhibitors or activators.

Analytical Chemistry: Boc-D-aspartic acid-β-tert-butyl ester is also used in analytical chemistry for the quantification and analysis of peptide samples. It serves as a reference standard or a calibration compound in various analytical techniques such as mass spectrometry and HPLC. This helps in ensuring the accuracy and reliability of analytical results in peptide research.

1. [Synthesis and 13C-NMR spectra of the N-terminal decapeptide sequence of human lymphoblast interferon]

G Jung, H Brückner Hoppe Seylers Z Physiol Chem. 1981 Mar;362(3):291-304.

The N-terminal sequence 1-10 of interferon HuIFN-alpha(Ly) from human lymphoblasts Ser-Asp-Leu-Pro-Gln-Thr-His-Ser-Leu-Gly (LIF[1-10]) was synthesized by the Merrifield method. N-tert-Butyloxycarbonylglycin was esterified via its cesium salt with a chloro-methylated polystyrene-1% divinylbenzene support yielding a loading of 0.3 mmol/g. Double couplings, each with a five-fold excess of N-protected amino acid, were performed with N,N'-dicyclohexylcarbodiimide and 1-hydroxybenzotriazole, followed by an acetylation step. N-tert-Butyloxycarbonyl-L-amino acids with O-benzyl protection for serine, threonine, and Nim-2,4-dinitrophenyl protection for histidine, and N-fluorenylmethyloxycarbonylaspartic acid beta-tert-butyl ester were used. N-tert-Butyloxycarbonyl-glutamine was coupled as 4-nitrophenyl ester in the presence of 1-hydroxybenzotriazole. The butyloxycarbonyl groups of the residues 3 to 10 were removed with trifluoroacetic acid in dichloromethane; the 9-fluorenylmethyloxycarbonyl group was split off with diethylamine. After quantitative hydrazinolysis in dimethylformamide, chromatography on Sephadex LH-20 with methanol and reversed-phase chromatography on silica gel RP-8 with methanol/water 9:1, the decapeptide hydrazide Boc-Ser(Bzl)-Asp(But)-Leu-Pro-Gln-Thr(Bzl)-His-Ser(Bzl)-Leu-Gly-NH-HN2 was isolated in pure state. The partially protected decapeptide was characterized by 13C-NMR spectroscopy, analysed, and linked with poly(L-lysine) (molecular mass 37 300) via its azide and also using m-xylylene diisocyanate. After a deprotection step the polylysine-LIF[1-10] antigens were dialyzed and lyophilized. Furthermore the free decapeptide LIF[1-10] was split-off from the resin using HBr/CF3CO2H, followed by mercaptoethanol treatment. After purification on Sephadex G-15 with 0.1 M acetic acid and on the reversed-phase silicagel RP-8 with methanol/water 9:1 water soluble LIF-[1-10] was obtained in pure state as shown by thin-layer-chromatography, electrophoreses amino acid analysis and 13C-NMR spectroscopy.

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%.