136497-85-3

Basic information

• Product Name: L-Serine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-, 2-propenyl ester
• CAS NO: 136497-85-3
• Molecular Formula: C21H21NO5
• Molecular Weight: 367.401
• Mol File: 136497-85-3.mol
• Article Data: 22

Chemical Properties

• CAS DataBase Reference: L-Serine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-, 2-propenyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Serine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-, 2-propenyl ester(136497-85-3)
• EPA Substance Registry System: L-Serine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-, 2-propenyl ester(136497-85-3)

Safety Data

• Hazardous Substances Data: 136497-85-3(Hazardous Substances Data)

Upstream product

• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 1030849-50-3 (S)-allyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(tert-butoxy)propanoate 
• 106-95-6 allyl bromide 
• 71989-33-8 Fmoc-Ser(tBu)-OH 
• 73724-45-5 N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine 

Downstream Products

• 155177-93-8 allyl N-(9-fluorenylmethoxycarbonyl)--(1<*>3)>-L-serine 
• 155177-92-7 allyl N-(-fluorenylmethoxycarbonyl)-3)>-L-serine 
• 221325-37-7 N-(9-fluorenylmethoxycarbonyl)-O-[(α,α-dimethyl-4-nitrobenzyl)dimethylsilyl]-L-serine allyl ester 
• 221325-43-5 N-(9-fluorenylmethoxycarbonyl)-O-[(4-amino-α,α-dimethylbenzyl)dimethylsilyl]-L-serine allyl ester 
• 221325-44-6 N-(9-fluorenylmethoxycarbonyl)-O-[(α,α-dimethyl-4-succin-monoamidobenzyl)dimethylsilyl]-L-serine allyl ester 
• 96383-44-7 O¹-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-N^α-(fluoren-9-ylmethoxycarbonyl)serine 
• 146936-87-0 (S)-3-((2S,3R,4R,5R,6R)-3-Azido-4-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid allyl ester 
• 187330-20-7 C₆₂H₆₈N₄O₂₀ 
• 187330-21-8 C₅₅H₆₄N₄O₂₀ 
• 155177-85-8 allyl N-(9-fluorenylmethoxycarbonyl)-[O-(2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-(1[*]3)]-L-serine 

Relevant articles and documents

Solid-phase parallel synthesis of functionalised medium-to-large cyclic peptidomimetics through three-component coupling driven by aziridine aldehyde dimers

The first solid-phase parallel synthesis of macrocyclic peptides using three-component coupling driven by aziridine aldehyde dimers is described. The method supports the synthesis of 9- to 18-membered aziridine-containing macrocycles, which are then functionalized by nucleophilic opening of the aziridine ring. This constitutes a robust approach for the rapid parallel synthesis of macrocyclic peptides. Solid-phase macrocycles: The first solid-phase parallel synthesis of macrocyclic peptides using three-component coupling driven by aziridine aldehyde dimers is described. The method supports the synthesis of 9- to 18-membered aziridine-containing macrocycles, which are then functionalised by nucleophilic opening of the aziridine ring (see scheme). This constitutes a robust approach for the rapid parallel synthesis of macrocyclic peptides.

Simplified Novel Muraymycin Analogues; using a Serine Template Strategy for Linking Key Pharmacophores

The present status of antibiotic research requires the urgent invention of novel agents that act on multidrug-resistant bacteria. The World Health Organization has classified antibiotic-resistant bacteria into critical, high and medium priority according to the urgency of need for new antibiotics. Naturally occurring uridine-derived “nucleoside antibiotics” have shown promising activity against numerous priority resistant organisms by inhibiting the transmembrane protein MraY (translocase I), which is yet to be explored in a clinical context. The catalytic activity of MraY is an essential process for bacterial cell viability and growth including that of priority organisms. Muraymycins are one subclass of naturally occurring MraY inhibitors. Despite having potent antibiotic properties, the structural complexity of muraymycins advocates for simplified analogues as potential lead structures. Herein, we report a systematic structure-activity relationship (SAR) study of serine template-linked, simplified muraymycin-type analogues. This preliminary SAR lead study of serine template analogues successfully revealed that the complex structure of naturally occurring muraymycins could be easily simplified to afford bioactive scaffolds against resistant priority organisms. This study will pave the way for the development of novel antibacterial lead compounds based on a simplified serine template.

Amino acid building blocks for efficient Fmoc solid-phase synthesis of peptides adenylylated at serine or threonine

The first straightforward building block based (non-interassembly) synthesis of peptides containing adenylylated serine and threonine residues is described. Key features include final global acidolytic protective group removal as well as full compatibility with standard Fmoc solid-phase peptide synthesis (SPPS). The described Thr-AMP SPPS-building block has been employed in the synthesis of the Thr-adenylylated sequence of human GTPase CDC42 (Ac-SEYVP-T(AMP)-VFDNYGC-NH2). Further, we demonstrate proof-of-concept for the synthesis of an Ser-adenylylated peptide (Ac-GSGA-S(AMP)-AGSGC-NH2) from the corresponding adenylylated serine building block.

Synthesis method and application of 1-aza -5-germanium-5-alkyl bicyclic [3.3.3] undecane compound.

The invention provides a 1-aza-5-germanium hetero-5-alkyl bicyclic [3.3.3] hendecane compound having a structure shown in the formula I, and the types of the 1-aza-5-germanium hetero-5-alkyl bicyclic[3.3.3] hendecane compound are expanded. The provided compound can serve as a nucleophilic reagent, the air and humidity conditions of the nucleophilic reagent are stable, and the efficiency of the Ge-Stille coupling reaction of aryl halogen and the 1-aza-5-germanium hetero-5-alkyl bicyclic [3.3.3] hendecane compound is high.