71989-14-5

Basic information

• Product Name: FMOC-L-Aspartic acid beta-tert-butyl ester
• Synonyms: Fmoc-(tBu)Asp-OH;cas:71989-14-5;Fmoc-L-aspartic acid β-tert-butyl ester≥ 99.7% (HPLC, Chiral purity);N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-L-ASPARTIC ACID BETA-T-BUTYL ESTER;N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-L-ASPARTIC ACID BETA-TERT-BUTYL ESTER;N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-L-ASPARTIC ACID BETA-T-BUTYL ESTER;N-9-FLUORENYLMETHYLOXYCARBONYL-L-ASPARTIC ACID BETA-T-BUTYL ESTER;N-9-FLUORENYLMETHYLOXYCARBONYL-L-ASPARTIC ACID BETA-TERT-BUTYL ESTER
• CAS NO: 71989-14-5
• Molecular Formula: C₂₃H₂₅NO₆
• Molecular Weight: 411.45
• EINECS: 276-251-7
• Product Categories: PROTECTED AMINO ACID & PEPTIDES;Amino Acids;Aspartic acid [Asp, D];Fmoc-Amino Acids and Derivatives;Amino Acids (N-Protected);Biochemistry;Fmoc-Amino Acids;Fmoc-Amino acid series
• Mol File: 71989-14-5.mol

Chemical Properties

• Melting Point: 148-150 °C (dec.)
• Boiling Point: 530.45°C (rough estimate)
• Flash Point: 329.3 °C
• Appearance: white to light yellow crystal powder
• Density: 1.2498 (rough estimate)
• Vapor Pressure: 2.83E-16mmHg at 25°C
• Refractive Index: -25 ° (C=1, DMF)
• Storage Temp.: 2-8°C
• PKA: 3.57±0.23(Predicted)
• Water Solubility: Slightly soluble in water.
• BRN: 3635671
• CAS DataBase Reference: FMOC-L-Aspartic acid beta-tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-L-Aspartic acid beta-tert-butyl ester(71989-14-5)
• EPA Substance Registry System: FMOC-L-Aspartic acid beta-tert-butyl ester(71989-14-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36/37/39-27-26
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 71989-14-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Fmoc-L-Aspartic acid beta-tert-butyl ester is used as a building block in the synthesis of peptides and proteins for various pharmaceutical applications. The Fmoc group allows for the stepwise assembly of peptide chains, while the beta-tert-butyl ester group protects the carboxylic acid group from unwanted side reactions during the synthesis process.
Used in Research and Development:
Fmoc-L-Aspartic acid beta-tert-butyl ester is used as a research tool in the development of new drugs and therapies. It can be incorporated into peptide-based drug candidates to study their biological activity and potential therapeutic effects.
Used in Biochemical Analysis:
Fmoc-L-Aspartic acid beta-tert-butyl ester can be used in biochemical assays and experiments to investigate the role of L-Aspartic acid in various biological processes, such as enzyme catalysis, metabolic pathways, and protein-protein interactions.
Used in Food and Beverage Industry:
Fmoc-L-Aspartic acid beta-tert-butyl ester can be used as a flavor enhancer in the food and beverage industry. L-Aspartic acid is known to enhance the taste of certain foods and beverages, and its derivatives, such as Fmoc-L-Aspartic acid beta-tert-butyl ester, can be used to achieve similar effects.
Used in Cosmetics Industry:
Fmoc-L-Aspartic acid beta-tert-butyl ester can be used in the development of cosmetic products, such as creams, lotions, and serums, to improve skin health and appearance. L-Aspartic acid is known to play a role in collagen synthesis, and its derivatives may have potential benefits for skin rejuvenation and anti-aging treatments.

InChI:InChI=1/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

Upstream product

• 88744-04-1 (9-fluorenyl)methyl pentafluorophenyl carbonate 
• 3057-74-7 L-Asp(t-Bu) 
• 99503-04-5 Carbonic acid 3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl ester 9H-fluoren-9-ylmethyl ester 
• 147221-34-9 Fmoc-Asp(OtBu)OPp 
• 56-84-8 L-Aspartic acid 
• 102774-86-7 9-fluorenylmethyl N-succinimidyl carbonate 
• 115-11-7 isobutene 
• 21715-90-2 N-hydroxy-5-norbornene-2,3-dicarboximide 
• 99502-89-3 Chlorameisensaeure-N-hydroxy-norborn-5-en-2,3-dicarboximidester 
• 144120-52-5 4-(1,1-dimethylethyl) ester of Nα-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-aspartic acid allyl ester 
• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 1334631-58-1 L-aspartic acid β-tert-butyl ester hydrochloride 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 

Downstream Products

• 71989-15-6 Fmoc-Asp(O-t-Bu)-ONp 
• 113534-20-6 Fmoc-Asp(OtBu)-OTDO 
• 86061-01-0 tert-butyl N-[(9H-fluoren-9-ylmethoxy)carbonyl]-1-pentafluorophenyl L-aspartate 
• 157886-16-3 Fmoc-Asp(Ot-Bu)-ODbn 
• 86061-07-6 Fmoc-Asp(t-Bu)-Phe-NH₂ 
• 110172-15-1 H-Tyr-Orn[*]-Phe-Asp[*]-NH₂ 
• 110116-75-1 H-Tyr-D-Asp[*]-Phe-A₂bu[*]-NH₂ 
• 110172-16-2 H-Tyr-D-Orn[*]-D-Phe-Asp[*]-NH₂ 
• 106327-80-4 H-Tyr-D-Orn[*]-Phe(NMe)-Asp[*]-NH₂ 
• 110116-74-0 H-Tyr-D-Orn[*]-Hfe-Asp[*]-NH₂ 
• 106327-79-1 H-Tyr-D-Orn[*]-Phe(p-NO₂)-D-Asp[*]-NH₂ 
• 110116-73-9 H-Tyr-D-Orn<*>-Phg-Asp<*>-NH2 
• 147221-34-9 Fmoc-Asp(OtBu)OPp 
• 143038-52-2 Fmoc-Asp(OtBu)-Leu-Lys(Boc)-Gly-OBzl 

Relevant articles and documents

COMPOUND FOR PREPARATION OF ANTIBODY-PAYLOAD CONJUGATE AND USE THEREOF

The present application relates to a novel linker for use in bioconjugation, comprising two or more electrophilic carbon atoms of a carbonyl group, and a click chemistry functional group and, more specifically, to a linker through which a compound, a peptide, and/or a protein can be directly and/or indirectly linked by a substitution reaction to a desired target molecule, that is, a target molecule.

Preparation method of N -fluorenylmethoxycarbonyl - L -aspartic -4 -tert-butyl ester

The invention relates to the technical field of organic synthesis, in particular to a preparation method of a fluorenylmethoxycarbonyl - aspartic -4 - tert-butyl ester, which comprises the following specific steps: L - aspartic acid is used as a starting raw material, L - aspartic acid internal anhydride hydrochloride is obtained through dehydration treatment of phosphorus trichloride. L- Aspartic acid ester hydrochloride and ethanol were subjected to alcoholysis to obtain L -aspartate hydrochloride. The transesterification reaction L-aspartate and tert-butyl ester gives L -butyl-1 -ethyl-4 -butyl acrylate. Further hydrolysis L-butyl-1 - ethyl ester -4 - gives L -butyl-4 -tert-butyl ester. The L-aspartate -4 - tert-butyl ester is reacted with the fluorenylmethoxycarbonyl reagent to obtain the target product fluorenylmethoxycarbonyl - aspartic -4 -tert-butyl ester. The preparation method of the fluorenylmethoxycarbonyl - aspartic -4 - tert-butyl ester provided by the invention is safe and environment-friendly in production process and suitable for industrial large-scale production.

Synthesis of l -octaarginine through microencapsulated palladium-catalyzed allyl ester deprotection

Octaarginine has been described as a molecular transporter. We report a useful synthesis of orthogonally protected l-octaarginine by using a method based on a microencapsulated palladium catalyst. Known palladium-based methods for allyl ester deprotection have been modified to facilitate purification of the unprotected intermediates. This improvement in the purification step has also been tested with a variety of allyl α-amino esters and allyl α,β-unsaturated esters.

A one-pot procedure for the preparation of N-9-fluorenylmethyloxycarbonyl- α-amino diazoketones from α-amino acids

The study describes a new "one-pot" route to the synthesis of N-9-fluorenylmethyloxycarbonyl (Fmoc) α-amino diazoketones. The procedure was tested on a series of commercially available free or side-chain protected α-amino acids employed as precursors. The conversion into the title compounds was achieved by masking and activating the α-amino acids with a single reagent, namely, 9-fluorenylmethyl chloroformate (Fmoc-Cl). The resulting N-protected mixed anhydrides were reacted with diazomethane to lead to the α-amino diazoketones, which were isolated by flash column chromatography in very good to excellent overall yields. The versatility of the procedure was verified on lipophilic α-amino acids and further demonstrated by the preparation of N-Fmoc-α-amino diazoketones also from α-amino acids containing side-chain masking groups, which are orthogonal to the Fmoc one. The results confirmed that tert-butyloxycarbonyl (Boc), tert-butyl (tBu), and 2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl (Pbf), three acid-labile protecting groups mostly adopted in the solution and solid-phase peptide synthesis, are compatible to the adopted reaction conditions. In all cases, the formation of the corresponding C-methyl ester of the starting amino acid was not observed. Moreover, the proposed method respects the chirality of the starting α-amino acids. No racemization occurred when the procedure was applied to the synthesis of the respective N-Fmoc-protected α-amino diazoketones from l-isoleucine and l-threonine and to the preparation of a diastereomeric pair of N-Fmoc-protected dipeptidyl diazoketones.

Efficient procedure for the preparation of oligomer-free N-fmoc amino acids

A two-step method is presented for the peptide-free, high-purity, and high-yield synthesis of N-Fmoc amino acids. The first step involves the preparation of stable dicyclohexylammonium-amino acid ionic adduct in acetone. Subsequently, the ionic adducts, on reaction with Fmoc-Nosu under mild alkaline conditions, give dipeptide-free N-Fmoc amino acids. The positive charge of the dicyclohexylammonium counterion in the ionic salt has a longer radius, moderating the nucleophilicity of the carboxylate ion of the amino acid and preventing by-products by arresting the formation of mixed anhydrides, the precursors of oligopeptide impurities.

GLP-2 compounds, formulations, and uses thereof

The present invention relates to novel human glucagon-like peptide-2 (GLP-2) peptides and human glucagon-like peptide-2 derivatives which have a protracted profile of action as well as polynucleotide constructs encoding such peptides, vectors and host cells comprising and expressing the polynucleotide, pharmaceutical compositions, uses and methods of treatment.

Synthesis of ω-tert-butyl esters of aspartic acid and glutamic acid via B,B-difluoroboroxazolidones

B,B-Difluoroboroxazolidones (DFBONs) were synthesized for the first time from salts of amino acid and BF3·Et2O, and their properties were examined. DFBONs were used in selective preparation of Glu(OBu(t)) and Asp(OBu(t)) in good yields under catalysis with BF3·Et2O and H3PO4. Amberlite XAD-2 resin was successfully employed to purify the above amino acid derivatives.

2-Phenyl isopropyl esters as carboxyl terminus protecting groups in the fast synthesis of peptide fragments

The esters of Fmoc aminoacids derived from 2-phenylisopropanol have been prepared by using 2-phenylisopropyltrichloroacetimidate 1. They prevent diketopiperazine formation during amino deprotection of dipeptides and can be cleaved in the presence of Boc and O-Bu(t). They are thus well suited for the protection of C-terminus when a fmoc strategy is used to build up peptide fragments.

A New Synthesis of Thymosin α1

Thymosin α1, an N-acetylated octacosa thymus peptide, isolated first from thymosin fraction 5, is synthesized by the solid phase method using the p-benzyloxybenzyl alcohol/polystyrene/divinylbenzene resin, Nα-Fmoc-amino acids and those with tert-butyl or Boc side chain protection.All couplings are performed with the Bop reagent.The peptide is purified by a combination of gel chromatography and preparative HPLC, its purity checked by amino acid analysis and analytical HPLC, and the biological activity tested by the E-rosette assay.