1354752-75-2

Basic information

• Product Name: (S)-2-{[((9H-fluoren-9-yl)methoxy)carbonyl]amino}-3-(prop-2-yn-1-yloxy)propanoic acid
• Synonyms: (S)-2-{[((9H-fluoren-9-yl)methoxy)carbonyl]amino}-3-(prop-2-yn-1-yloxy)propanoic acid
• CAS NO: 1354752-75-2
• Molecular Weight: 365.386
• Mol File: 1354752-75-2.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: (S)-2-{[((9H-fluoren-9-yl)methoxy)carbonyl]amino}-3-(prop-2-yn-1-yloxy)propanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-{[((9H-fluoren-9-yl)methoxy)carbonyl]amino}-3-(prop-2-yn-1-yloxy)propanoic acid(1354752-75-2)
• EPA Substance Registry System: (S)-2-{[((9H-fluoren-9-yl)methoxy)carbonyl]amino}-3-(prop-2-yn-1-yloxy)propanoic acid(1354752-75-2)

Safety Data

• Hazardous Substances Data: 1354752-75-2(Hazardous Substances Data)

Usage

General Description

The chemical "(S)-2-{[((9H-fluoren-9-yl)methoxy)carbonyl]amino}-3-(prop-2-yn-1-yloxy)propanoic acid" is a compound consisting of a fluorenylmethoxycarbonyl (Fmoc) protecting group attached to an amino acid derivative. It also contains a prop-2-yn-1-yloxy (POM) protecting group attached to the amino acid. The Fmoc group is commonly used in peptide chemistry for protecting the amine group during synthesis, while the POM group is used to protect the hydroxyl group of serine or threonine. (S)-2-{[((9H-fluoren-9-yl)methoxy)carbonyl]amino}-3-(prop-2-yn-1-yloxy)propanoic acid is likely used in the synthesis of peptides and other biological molecules where precise control of reactivity and protection of functional groups is necessary.

Upstream product

• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 1379150-93-2 O-propargyl-L-serine hydrochloride 
• 497-19-8 sodium carbonate 
• 675585-14-5 N-[(1,1-dimethylethoxy)carbonyl]-O-(prop-2-yn-1-yl)serine methyl ester 
• 145205-94-3 (S)-2-[(tert-butoxycarbonyl)amino]-3-(prop-2-yn-1-yloxy)propanoic acid 

Downstream Products

• 1558028-97-9 C₃₈H₅₅N₁₁O₁₁ 
• 1558028-92-4 C₃₂H₄₄N₈O₆ 

Relevant articles and documents

Drug Design Inspired by Nature: Crystallographic Detection of an Auto-Tailored Protease Inhibitor Template

De novo drug discovery is still a challenge in the search for potent and selective modulators of therapeutically relevant target proteins. Here, we disclose the unexpected discovery of a peptidic ligand 1 by X-ray crystallography, which was auto-tailored by the therapeutic target MMP-13 through partial self-degradation and subsequent structure-based optimization to a highly potent and selective β-sheet peptidomimetic inhibitor derived from the endogenous tissue inhibitors of metalloproteinases (TIMPs). The incorporation of non-proteinogenic amino acids in combination with a cyclization strategy proved to be key for the de novo design of TIMP peptidomimetics. The optimized cyclic peptide 4 (ZHAWOC7726) is membrane permeable with an IC50 of 21 nm for MMP-13 and an attractive selectivity profile with respect to a polypharmacology approach including the anticancer targets MMP-2 (IC50: 170 nm) and MMP-9 (IC50: 140 nm).

Hierarchical supramolecular hydrogels: Self-assembly by peptides and photo-controlled release: Via host-guest interaction

A hierarchical supramolecular hydrogel was self-assembled from a Fmoc-RGDS tetrapeptide and showed photo-controlled release directed by host-guest interaction. Multiple payloads, including vesicles, were successively released from a single peptide hydrogel.

Oxidative α,ω-diyne coupling as an approach towards novel peptidic macrocycles

The Glaser-Hay diyne coupling proved to be an efficient cyclisation approach towards diyne containing peptidic macrocycles. A variety of tetrapeptide-based macrocyclic 1,3-diynes were obtained from O-propargylated serine or tyrosine residues using Cu(OAc)2·H2O and NiCl2 under an O2-atmosphere. The effect of the linear 1,3-diyne on peptide conformations was studied by NMR and compared with a macrocycle bearing a saturated linker.