288617-74-3

Basic information

• Product Name: (S)-N-FMoc-2-(5'-pentenyl)alanine
• Synonyms: (S)-N-FMoc-2-(5'-pentenyl)alanine;(S)-2-((((9H-Fluoren-9-yl)Methoxy)carbonyl)aMino)-2-Methyloct-7-enoic acid;(S)-N-FMoc-2-(5'-hexenyl)alanine;FMoc-α-Me-Gly(Hexenyl)-OH;(S)-N-Fmoc-2-(5'-hexyl)alanine;(9H-Fluoren-9-yl)MethOxy]Carbonyl Alpha-Methyl-Gly(Hexenyl)-OH
• CAS NO: 288617-74-3
• Molecular Formula: C24H27NO4
• Molecular Weight: 393.47548
• Mol File: 288617-74-3.mol

Chemical Properties

• Boiling Point: 605.3±55.0 °C(Predicted)
• Appearance: /
• Density: 1.169±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 3.94±0.41(Predicted)
• CAS DataBase Reference: (S)-N-FMoc-2-(5'-pentenyl)alanine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-N-FMoc-2-(5'-pentenyl)alanine(288617-74-3)
• EPA Substance Registry System: (S)-N-FMoc-2-(5'-pentenyl)alanine(288617-74-3)

Safety Data

• Hazardous Substances Data: 288617-74-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Chemistry:
(S)-N-FMoc-2-(5'-pentenyl)alanine is used as a building block for the synthesis of complex organic molecules, leveraging its Fmoc protection and pentenyl side chain for versatile chemical reactions.
Used in Medicinal Chemistry:
(S)-N-FMoc-2-(5'-pentenyl)alanine is utilized as a key component in the development of novel therapeutic agents, taking advantage of its unique structural features to create bioactive peptides and drug candidates.
Used in Solid-Phase Peptide Synthesis:
(S)-N-FMoc-2-(5'-pentenyl)alanine is used as a protected amino acid in solid-phase peptide synthesis, where its Fmoc group plays a critical role in preventing side reactions and ensuring the successful assembly of peptide sequences.
Used in Drug Development:
(S)-N-FMoc-2-(5'-pentenyl)alanine is employed as a starting material for the design and synthesis of innovative drugs, capitalizing on its pentenyl side chain for further chemical modifications and functionalization to achieve desired pharmacological properties.
Used in Research:
(S)-N-FMoc-2-(5'-pentenyl)alanine is utilized as a research tool to study the structure-activity relationships of peptides and to explore the potential of novel peptide-based therapeutics in various biological assays and disease models.

Upstream product

• 1445137-81-4 (S)-2-(benzyloxycarbonylamino)-2-methyloct-7-enoic acid 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 18922-04-8 6-iodohex-1-ene 
• 84418-43-9 9-fluorenylmethyl carbamate 

Downstream Products

• 1445137-70-1 C₈₀H₁₂₂N₁₈O₁₄ 

Relevant articles and documents

Design of cell-permeable stapled peptides as HIV-1 integrase inhibitors

HIV-1 integrase (IN) catalyzes the integration of viral DNA into the host genome, involving several interactions with the viral and cellular proteins. We have previously identified peptide IN inhibitors derived from the α-helical regions along the dimeric interface of HIV-1 IN. Herein, we show that appropriate hydrocarbon stapling of these peptides to stabilize their helical structure remarkably improves the cell permeability, thus allowing inhibition of the HIV-1 replication in cell culture. Furthermore, the stabilized peptides inhibit the interaction of IN with the cellular cofactor LEDGF/p75. Cellular uptake of the stapled peptide was confirmed in four different cell lines using a fluorescein-labeled analogue. Given their enhanced potency and cell permeability, these stapled peptides can serve as not only lead IN inhibitors but also prototypical biochemical probes or nanoneedles for the elucidation of HIV-1 IN dimerization and host cofactor interactions within their native cellular environment.