200335-75-7

Basic information

• Product Name: Fmoc-D-Asp(OtBu)-Opfp
• Synonyms: (R)-4-tert-butyl 1-perfluorophenyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)succinate;Fmoc-D-aspartic acid beta-tert-butyl ester alpha-pentafluorophenyl ester;N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-D-aspartic acid 4-(1,1-dimethylethyl) 1-(pentafluorophenyl) ester;(9H-Fluoren-9-yl)MethOxy]Carbonyl D-Asp(OtBu)-Opfp
• CAS NO: 200335-75-7
• Molecular Formula: C29H24F5NO6
• Molecular Weight: 577.5
• Mol File: 200335-75-7.mol

Chemical Properties

• Boiling Point: 665.98°C at 760 mmHg
• Flash Point: 356.572°C
• Appearance: /
• Density: 1.373g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.547
• Storage Temp.: Store at 0°C
• PKA: 9.75±0.46(Predicted)
• CAS DataBase Reference: Fmoc-D-Asp(OtBu)-Opfp(CAS DataBase Reference)
• NIST Chemistry Reference: Fmoc-D-Asp(OtBu)-Opfp(200335-75-7)
• EPA Substance Registry System: Fmoc-D-Asp(OtBu)-Opfp(200335-75-7)

Safety Data

• Hazardous Substances Data: 200335-75-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Fmoc-D-Asp(OtBu)-Opfp is used as a building block for the synthesis of peptides and peptide-based drugs. Its protected structure allows for the incorporation of D-aspartic acid into peptide sequences without unwanted side reactions, which is essential for the development of therapeutic agents with specific biological activities.
Used in Research and Development:
In the field of peptide research, Fmoc-D-Asp(OtBu)-Opfp serves as a key component for the synthesis of novel peptide sequences. It enables scientists to explore the properties and functions of D-amino acid-containing peptides, which can lead to the discovery of new bioactive molecules and potential drug candidates.
Used in Peptide Synthesis Education:
Fmoc-D-Asp(OtBu)-Opfp is also utilized in educational settings to teach the principles of peptide synthesis and the use of protecting groups. By incorporating this compound into laboratory exercises, students can gain hands-on experience in the synthesis of peptides and understand the importance of protecting groups in the process.
Overall, Fmoc-D-Asp(OtBu)-Opfp plays a significant role in various applications across the pharmaceutical, research, and educational sectors, primarily due to its ability to facilitate the controlled synthesis of peptides containing D-aspartic acid.

InChI:InChI=1/C29H24F5NO6/c1-29(2,3)41-20(36)12-19(27(37)40-26-24(33)22(31)21(30)23(32)25(26)34)35-28(38)39-13-18-16-10-6-4-8-14(16)15-9-5-7-11-17(15)18/h4-11,18-19H,12-13H2,1-3H3,(H,35,38)/t19-/m1/s1

Upstream product

• 14533-84-7 pentafluorophenyl trifloroacetate 
• 71989-14-5 Fmoc-(tBu)Asp-OH 
• 3057-74-7 L-Asp(t-Bu) 
• 771-61-9 2,3,4,5,6-pentafluorophenol 
• 71989-14-5 N-(9-fluorenylmethoxycarbonyl)-4-O-tert-butyl-D-aspartic acid 
• 88744-04-1 (9-fluorenyl)methyl pentafluorophenyl carbonate 

Downstream Products

• 1947-37-1 cholecystokinin-4 
• 797751-68-9 N^α-Fmoc-L-Asn-OPfp 
• 155238-94-1 SKF 107647 
• 133565-45-4 (S)-tert-butyl 3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-hydroxybutanoate 
• 920519-32-0 Fmoc-D-Asp(tBu)-D-Thr(Ψ^MeMepro)-OH 

Relevant articles and documents

4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium Toluene-4-sulfonate (DMT/NMM/TsO?) Universal Coupling Reagent for Synthesis in Solution

4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium toluene-4-sulfonate (DMT/NMM/TsO?), a representative member of the inexpensive and environmentally-friendly N-triazinylammonium family of sulfonates, has been found to be a very effective coupling reagent for the synthesis of amides, esters and peptides in solution. This study confirms the usefulness of DMT/NMM/TsO? for peptide synthesis in solution, starting from Z-, Fmoc-, and Boc-protected substrates as well as unnatural building blocks. Peptide synthesis with DMT/NMM/TsO? produced high yields, with high crude product purity and low risk of racemization. In all cases, stoichiometric amounts of reagents were used and the standard synthetic procedure, without the need for time-consuming optimization stages or expensive chromatographic purification. DMT/NMM/TsO? was also found to be very useful for the synthesis of oligopeptides using a fragment coupling strategy.

Total Chemical Synthesis and Folding of All- l and All- d Variants of Oncogenic KRas(G12V)

The Ras proteins are essential GTPases involved in the regulation of cell proliferation and survival. Mutated oncogenic forms of Ras alter effector binding and innate GTPase activity, leading to deregulation of downstream signal transduction. Mutated forms of Ras are involved in approximately 30% of human cancers. Despite decades of effort to develop direct Ras inhibitors, Ras has long been considered "undruggable" due to its high affinity for GTP and its lack of hydrophobic binding pockets. Herein, we report a total chemical synthesis of all-l- and all-d-amino acid biotinylated variants of oncogenic mutant KRas(G12V). The protein is synthesized using Fmoc-based solid-phase peptide synthesis and assembled using combined native chemical ligation and isonitrile-mediated activation strategies. We demonstrate that both KRas(G12V) enantiomers can successfully fold and bind nucleotide substrates and binding partners with observable enantiodiscrimination. By demonstrating the functional competency of a mirror-image form of KRas bound to its corresponding enantiomeric nucleotide triphosphate, this study sets the stage for further biochemical studies with this material. In particular, this protein will enable mirror-image yeast surface display experiments to identify all-d peptide ligands for oncogenic KRas, providing a useful tool in the search for new therapeutics against this challenging disease target.

P-toluenosulfonate salt of N-Methyl-N-(3,5-dimathoxy-2,4,6-triazinyl-1-)-morpholine and related compounds for use as condensing reagent in peptide synthesis

The invention refers to new quarternary N-(3,5-disubstituted-1,3,5-triazinyl-1)-ammonium salts of sulfonic acids, with formula 1, where R1 and R2 denote in total or independently a halogen atom, an alkyl group, a substituted alkyl gr

N-triazinylammonium tetrafluoroborates. A new generation of efficient coupling reagents useful for peptide synthesis

A new generation of triazine-based coupling reagents (TBCRs), designed according to the concept of "superactive esters", was obtained by treatment of 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium (DMTMM) chloride with lithium or silver tetrafluoroborate. The structure of 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium tetrafluoroborate was confirmed by X-ray diffraction. Activation of carboxylic acids by using this reagent proceeds via triazine "superactive ester". The coupling reagent was successfully used for the synthesis of Z-, Boc-, and Fmoc-protected dipeptides derived from natural and unnatural sterically hindered amino acids and for fragment condensation, in 80-100% yield and with high enantiomeric purity. The manual SPPS of the ACP(65-74) peptide fragment (H-Val-Gln-Ala-Ala- lle-Asp-Tyr-Ile-Asn-Gly-OH) proceeded significantly faster than with TBTU or HATU, as well as the automated SPPS of the same fragment gave a purer product than by using TBTU or PyBOP. The reagent was also demonstrated to be efficient in on-resin head-to-tail cyclization of constrained cyclopeptides, in SPPS synthesis of Aib peptides, and in the synthesis of esters from appropriate acids, alcohols, and phenols. The high efficiency and versatility of this new generation of TBCRs confirm, for the first time, the usefulness of the concept of "superactive esters" in rational design of the structure of coupling reagents.

In vitro and in vivo evaluations of THAM derived telomers bearing RGD and Ara-C for tumour neovasculature targeting

As an approach to the development of specific drug delivery systems, a new class of low macromolecular carriers called 'telomers' endowed with an antitumour agent, such as arabinofuranosylcytosine (Ara-C), RGDSK peptidic sequences, as tumour targeting moieties, and tyrosine groups labelled with 125I atoms allowing the in vivo scintigraphic follow up, were synthesized. Their tumour targeting ability was assessed in vivo in mice bearing a murine B16 melanoma. The biological results showed that the presence of RGDSK sequences onto the macromolecules leads to the selective targeting and the accumulation of telomers within the vascularized zone of the tumour. Moreover, such compounds exhibited in vitro a better IC50 (0.015 μM) than pure Ara-C and in vivo an oncostatic index higher than 160%.

Preparation of glycosyl amino acids as building blocks for the combinatorial synthesis of neoglycoconjugates

Several neoglycosyl amino acids possessing a sugar residue, a spacer and a trifunctional amino acid moiety were synthesized both in solution and solid phase by activating the carboxylic group as its pentafluorophenyl ester for condensation. The methodolog

PREPARATION OF PENTAFLUOROPHENYL ESTERS OF FMOC PROTECTED AMINO ACIDS WITH PENTAFLUOROPHENYL TRIFLUOROACETATE

A high yield procedure for the preparation of pentafluorophenyl esters of Nα-9-fluorenylmethyloxycarbonyl protected amino acids is described.The procedure utilizes pentafluorophenyl trifluoroacetate.

9-Fluorenylmethyl Pentafluorophenyl Carbonate as a Useful Reagent for the Preparation of N-9-Fluorenylmethyloxycarbonylamino Acids and their Pentafluorophenyl Esters

9-Fluorenylmethyl pentafluorophenyl carbonate is a useful reagent for the efficient, side reaction-free introduction of N-9-fluorenylmethyloxycarbonyl protecting group into amino acids and for the subsequent preparation of their pentafluorophenyl esters.Some new compounds of both types are described.