129460-09-9

Basic information

• Product Name: L-Fmoc-Aspartic acid alpha-tert-butyl ester
• Synonyms: Fmoc-L-aspartic acid 1-tert-butyl ester;1-tert-Butyl N-Fmoc-L-aspartate;N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-aspartic Acid 1-tert-Butyl Ester;N-Fmoc-L-aspartic Acid 1-tert-Butyl Ester;Fmoc-Asp(OH)-OtBu;Fmoc-Asp(OtBu)-OH ,99%;N-Fmoc-L-aspartic Ac;FMOC-ASP-OTBU ( L isomer )
• CAS NO: 129460-09-9
• Molecular Formula: C₂₃H₂₅NO₆
• Molecular Weight: 411.45
• Product Categories: Amino Acids;Aspartic acid [Asp, D];Fmoc-Amino Acids and Derivatives;Fmoc-Amino acid series
• Mol File: 129460-09-9.mol
• Article Data: 7

Chemical Properties

• Melting Point: 90-98°C
• Boiling Point: 617.4 °C at 760 mmHg
• Flash Point: 327.2 °C
• Appearance: /
• Density: 1.251 g/cm³
• Vapor Pressure: 4.21E-16mmHg at 25°C
• Refractive Index: 1.576
• Storage Temp.: Store at RT.
• PKA: 4.08±0.19(Predicted)
• CAS DataBase Reference: L-Fmoc-Aspartic acid alpha-tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Fmoc-Aspartic acid alpha-tert-butyl ester(129460-09-9)
• EPA Substance Registry System: L-Fmoc-Aspartic acid alpha-tert-butyl ester(129460-09-9)

Safety Data

• Safety Statements: 24/25
• WGK Germany: WGK 2 water endangering
• HazardClass: IRRITANT
• Hazardous Substances Data: 129460-09-9(Hazardous Substances Data)

Usage

Description

L-Fmoc-Aspartic acid alpha-tert-butyl ester, commonly known as Fmoc-Asp-OtBu, is an amino acid building block that plays a crucial role in peptide synthesis. It is a white powder with specific chemical properties that make it a valuable component in the development of peptide-based drugs and therapies.

Uses

Used in Pharmaceutical Industry:
L-Fmoc-Aspartic acid alpha-tert-butyl ester is used as a key building block for the synthesis of peptides, which are essential in the development of various pharmaceutical products. The growing peptide drug market highlights the importance of fast and reliable peptide synthesis, making Fmoc-Asp-OtBu a valuable asset in this industry.
Used in Research and Development:
In the field of research and development, L-Fmoc-Aspartic acid alpha-tert-butyl ester is utilized for the synthesis of novel peptides with potential therapeutic applications. Its role in peptide synthesis allows researchers to explore new avenues in drug discovery and development, contributing to the advancement of medical science.
Used in Drug Delivery Systems:
Similar to gallotannin, L-Fmoc-Aspartic acid alpha-tert-butyl ester can be employed in the development of drug delivery systems, particularly for peptide-based drugs. These systems aim to improve the delivery, bioavailability, and therapeutic outcomes of peptide drugs, enhancing their overall efficacy in treating various medical conditions.

InChI:InChI=1/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-/m0/s1

Upstream product

• 540-88-5 acetic acid tert-butyl ester 
• 150009-58-8 9-fluorenylmethoxycarbonyl-O-benzyl-L-aspartic acid 
• 168261-64-1 (S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)succinic acid 4-benzyl ester 1-tert-butyl ester 
• 56-84-8 L-Aspartic acid 
• 102774-86-7 9-fluorenylmethyl N-succinimidyl carbonate 
• 115-11-7 isobutene 

Downstream Products

• 136083-57-3 N-α-9-fluorenylmethoxycarbonyl-aspartic acid 
• 708269-66-3 3-{2-[3-tert-butoxycarbonyl-2-(2-tritylsulfanyl-acetylamino)-propionyl amino]-2-carboxy-ethyl}-indole-1-carboxylic acid tert-butyl ester 
• 1352039-29-2 C₃₂H₃₄N₂O₁₀ 
• 623901-60-0 L-Phe-β-L-Asp-GlyOH 
• 1251908-99-2 D-Phe-β-L-Asp-GlyOH 
• 623901-63-3 Gly-β-L-Asp-L-PheOH 
• 131287-39-3 N^ω-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-N^α-(9-fluorenylmethyloxycarbonyl))-L-asparagine 
• 1268524-65-7 (S)-tert-butyl 3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-((3-(4-chlorobenzoyl)-4,5-dimethylthiophen-2-yl)amino)-4-oxobutanoate 

Relevant articles and documents

Application of tert-Butyl Disulfide-Protected Amino Acids for the Fmoc Solid-Phase Synthesis of Lactam Cyclic Peptides under Mild Metal-Free Conditions

Lactam cyclic peptides are a class of interesting and pharmaceutically active molecules, but their previous syntheses have required the use of heavy metals and/or forcing conditions. Here, we describe the efficient application of the previously reported tert-butyl disulfide-protected amino acids and their use in the efficient, solid-phase synthesis of a series of lactam cyclic peptides under mild, metal-free conditions.

Highly reactive and chemoselective cleavage of allyl esters using an air- and moisture-stable [CpRu(IV)(π-C3H5)(2-quinolinecarboxylato)]PF6 catalyst

A new catalytic process for allyl ester cleavage has been developed by using a robust cationic CpRu(IV) π-allyl complex of 2-quinolinecarboxylic acid that can be stored for over six months in air without any loss of catalytic activity. The deprotection of various alcohols and acids can be attained simply with high reactivity and chemoselectivity under mild conditions. Furthermore, with continuous removal of the low-boiling point coproduct, a turnover number of 1 000 000 can be achieved.

(P(C6H5)3)CpRu+-catalyzed deprotection of allyl carboxylic esters

A new and efficient catalytic method for deprotection of allyl carboxylic esters using a transition metal complex is reported. The reaction proceeds with a high substrate/catalyst ratio and without use of additional nucleophiles, giving the deprotected carboxylic acid in a quantitative yield. A variety of substrates, including the multifunctional amino acids and peptides, are also usable. The new method is more efficient, safe, and operationally simple in comparison to the conventional palladium-catalyzed method.