477578-53-3

Basic information

• Product Name: (S)-2-FMOC-AMINO-PENT-4-ENOIC ACID BENZYL ESTER
• Synonyms: (S)-2-FMOC-AMINO-PENT-4-ENOIC ACID BENZYL ESTER
• CAS NO: 477578-53-3
• Molecular Formula: C₂₇H₂₅NO₄
• Molecular Weight: 427.49
• Mol File: 477578-53-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-2-FMOC-AMINO-PENT-4-ENOIC ACID BENZYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-FMOC-AMINO-PENT-4-ENOIC ACID BENZYL ESTER(477578-53-3)
• EPA Substance Registry System: (S)-2-FMOC-AMINO-PENT-4-ENOIC ACID BENZYL ESTER(477578-53-3)

Safety Data

• Hazardous Substances Data: 477578-53-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
(S)-2-FMOC-AMINO-PENT-4-ENOIC ACID BENZYL ESTER is used as a building block for the synthesis of peptides and other organic molecules, playing a crucial role in the development of new pharmaceutical compounds. Its ability to be incorporated into peptide structures allows for the creation of novel drug candidates with potential therapeutic applications.
Used in Biochemical Research:
In biochemical research, (S)-2-FMOC-AMINO-PENT-4-ENOIC ACID BENZYL ESTER is used as a reagent for labeling and modifying proteins and peptides. This enables scientists to study the structure, function, and interactions of these biomolecules, leading to a better understanding of biological processes and the development of targeted therapies.
Used in Solid-Phase Peptide Synthesis:
(S)-2-FMOC-AMINO-PENT-4-ENOIC ACID BENZYL ESTER is used as a key component in solid-phase peptide synthesis, a widely employed technique for the production of peptides and proteins. Its Fmoc protecting group facilitates the stepwise assembly of peptide chains, allowing for precise control over the synthesis process and the creation of complex peptide structures.
Used in Chemical Synthesis:
(S)-2-FMOC-AMINO-PENT-4-ENOIC ACID BENZYL ESTER is also used in various chemical synthesis applications, where its unique structure and functional groups can be exploited to produce a range of valuable compounds with diverse properties and potential applications in industries such as materials science, agriculture, and environmental science.

Upstream product

• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 16338-48-0 L-allylglycine 
• 100-39-0 benzyl bromide 
• 146549-21-5 2-(9H-fluoren-9-ylmethoxycarbonylamino)-pent-4-enoic acid 

Downstream Products

• 61549-47-1 dec-5-ene-2,9-dione 
• 276869-41-1 2-(9H-fluoren-9-ylmethoxycarbonylamino)-octanedioic acid 8-tert-butyl ester 
• 159751-47-0 (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-6-(tert-butoxy)-6-oxohexanoic acid 
• 868754-94-3 6-(9H-fluoren-9-ylmethoxycarbonylamino)-hept-3-enedioic acid 7-benzyl ester 1-tert-butyl ester 
• 868754-95-4 2-(9H-fluoren-9-ylmethoxycarbonylamino)-oct-4-enedioic acid 1-benzyl ester 8-tert-butyl ester 
• 868754-93-2 5-(9H-fluoren-9-ylmethoxycarbonylamino)-hex-2-enedioic acid 6-benzyl ester 1-tert-butyl ester 

Relevant articles and documents

Divergent Access to Histone Deacetylase Inhibitory Cyclopeptides via a Late-Stage Cyclopropane Ring Cleavage Strategy. Short Synthesis of Chlamydocin

A unified step-economical strategy for accessing histone deacetylase inhibitory peptides is proposed, based on the late-stage installation of multiple zinc-binding functionalities via the cleavage of the strained cyclopropane ring in the common pluripoten

FMOC PROTECTED (2S)-2-AMINO-8-[(1,1-DIMETHYLETHOXY)AMINO]-8-OXO-OCTANOIC ACID, (S)-2-AMINO-8-OXONONANOIC ACID AND (S)-2-AMINO-8-OXODECANOIC ACID FOR PEPTIDE SYNTHESIS

The invention discloses Fmoc protected (2S)-2-amino-8-[(1,1- dimethylethoxy)amino]-8-oxo-octanoic acid, (S)-2-amino-8- oxononanoic acid and (S)-2-amino-8-oxodecanoic acid for use in peptide synthesis, such as solid phase synthesis, as well as the peptide H3K27 (Ac-Lys-Ala-Ala-Arg-Aox-Ser-Ala-NH2) prepared from Fmoc protected (2S)-2-amino-8-[(1,1-dimethylethoxy)amino]-8-oxo-octanoic acid (Aox). These three exemplary compounds as well as their unprotected forms are claimed in the form of four generic formulae. The first of these four formulae is (formula (I)) where -NPro is a protected amino group, such as an amino group protected with a base-labile protecting group, -L- is alkylene, heteroalkylene, arylene or aralkylene, -X- is a covalent bond, -N(H) - or -N(RN)-, where -RN is alkyl, -R2 is hydrogen or alkyl, -R3 is alkyl, such as C2-10 alkyl, or heterocyclyl, and -LAA- and -R1 are as defined in the claims.

Rational Drug Design of Topically Administered Caspase 1 Inhibitors for the Treatment of Inflammatory Acne

The use of an interleukin β antibody is currently being investigated in the clinic for the treatment of acne, a dermatological disorder affecting 650M persons globally. Inhibiting the protease responsible for the cleavage of inactive pro-IL1β into active IL-1β, caspase-1, could be an alternative small molecule approach. This report describes the discovery of uracil 20, a potent (38 nM in THP1 cells assay) caspase-1 inhibitor for the topical treatment of inflammatory acne. The uracil series was designed according to a published caspase-1 pharmacophore model involving a reactive warhead in P1 for covalent reversible inhibition and an aryl moiety in P4 for selectivity against the apoptotic caspases. Reversibility was assessed in an enzymatic dilution assay or by using different substrate concentrations. In addition to classical structure-activity-relationship exploration, topical administration challenges such as phototoxicity, organic and aqueous solubility, chemical stability in solution, and skin metabolic stability are discussed and successfully resolved.

Convenient access to glutamic acid side chain homologues compatible with solid phase peptide synthesis

(Chemical Equation Presented) Preparation of several side chain length variants of glutamic acid is achieved via olefin cross metathesis of allyl glycine derivatives. The products are suitably protected for direct use in Fmoc solid-phase peptide synthesis, as demonstrated by successful synthesis of test sequences.