71460-02-1

Basic information

• Product Name: (2S)-2-[[(1,1-Dimethylethoxy)carbonyl]amino]-4-pentynoic acid methyl ester
• Synonyms: (2S)-2-[[(1,1-Dimethylethoxy)carbonyl]amino]-4-pentynoic acid methyl ester;(S)-2-(Boc-amino)-4-pentynoic acid methyl ester;Methyl (2S)-2-(tert-butoxycarbonylamino)pent-4-ynoate
• CAS NO: 71460-02-1
• Molecular Formula: C₁₁H₁₇NO₄
• Molecular Weight: 227.25698
• Mol File: 71460-02-1.mol
• Article Data: 25

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (2S)-2-[[(1,1-Dimethylethoxy)carbonyl]amino]-4-pentynoic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-2-[[(1,1-Dimethylethoxy)carbonyl]amino]-4-pentynoic acid methyl ester(71460-02-1)
• EPA Substance Registry System: (2S)-2-[[(1,1-Dimethylethoxy)carbonyl]amino]-4-pentynoic acid methyl ester(71460-02-1)

Safety Data

• Hazardous Substances Data: 71460-02-1(Hazardous Substances Data)

Usage

General Description

(2S)-2-[[(1,1-Dimethylethoxy)carbonyl]amino]-4-pentynoic acid methyl ester, also known as Fmoc-L-homopropargylglycine methyl ester, is a chemical compound often used in bioconjugation reactions. It is a derivative of the amino acid glycine and contains a homopropargyl group, making it a valuable building block for the synthesis of diverse peptide and protein conjugates. The Fmoc protecting group enables selective deprotection and subsequent functionalization of the compound for specific applications. This chemical also possesses alkynyl functionality, which makes it useful for click chemistry, a popular method for bioconjugation. Overall, the compound has significant potential for use in various research fields, such as drug development, chemical biology, and materials science.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 70837-20-6 propargyclycine methyl ester hydrochloride 
• 166271-28-9 (S)-1-methoxy-1-oxopent-4-yn-2-aminium chloride 
• 67-56-1 methanol 
• 23235-01-0 (2S)-2-amino-4-pentynoic acid 
• 186581-53-3 diazomethane 
• 61172-66-5 (S)-2-(tert-butoxycarbonylamino)pent-4-ynoic acid 
• 101925-55-7 (S)-propargylglycine methyl ester 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 151139-90-1 (4S)-2,2-dimethyl-4-prop-2'-ynyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 763122-73-2 (2S)-2-tert-butoxycarbonylamino-pent-4-yn-1-ol 
• 74-88-4 methyl iodide 
• 23235-02-1 N-Acetyl-α-propargylglycine 
• 61172-66-5 2-((tert-butoxycarbonyl)amino)pent-4-ynoic acid 

Downstream Products

• 540516-91-4 methyl 5-(2-aminophenyl)-2-[(tert-butoxycarbonyl)amino]-4-pentynoate 
• 291533-78-3 Methyl 2-N-boc-amino-5-(4-morpholinophenyl)-pent-4-ynoate 
• 540516-97-0 4-[3-(2-aminophenyl)-2-propynyl]-1,3-oxazolidin-2-one 
• 540516-93-6 1-(tert-butyl) 2-methyl 5-(2-aminophenyl)-2,3-dihydro-1H-1,2-pyrroledicarboxylate 
• 548761-42-8 [4-(2-amino-phenyl)-1-hydroxymethyl-but-3-ynyl]-carbamic acid tert-butyl ester 
• 90600-20-7 (2S)-2-[(tert-butoxycarbonyl)amino]pent-4-enoic acid 
• 111836-35-2 5-phenyl-3,4-dihydro-2H-pyrrole-2-carboxylate de methyle 
• 955-81-7 methyl 5-(4-methoxyphenyl)-3,4-dihydro-2H-2-pyrrolecarboxylate 

Relevant articles and documents

Stable cyclopropene-containing analogs of the amino acid neurotransmitter glutamate

As a neurotransmitter, the amino acid glutamate has been the subject of efforts to generate structural analogs with unique properties. Here we report a practical, half-gram synthesis of two cyclopropene-containing glutamate analogs. These analogs are stable in solution, in the presence of the biological nucleophile glutathione, upon concentration, and during long-term storage, while maintaining their amenability to photo- or enzyme-caging and reactivity with bioorthogonal reaction partners like s-tetrazine or light-activated tetrazoles.

Design, synthesis and biological evaluation of C(4) substituted monobactams as antibacterial agents against multidrug-resistant Gram-negative bacteria

A series of novel pyridone conjugated monobactams with various substituents at the (4) position were synthesized and evaluated for their antibacterial activities against a panel of multidrug-resistant (MDR) Gram-negative bacteria in vitro. Compounds 46d, 54 and 75e displayed good to moderate activities against P. aeruginosa, among which the activity of 75e against P. aeruginosa was comparable to that of BAL30072 under iron limitation condition. Compounds 35, 46d, 54, 56a, 56c and 56d exhibited good to excellent antibacterial activities against E. coli and K. pneumoniae, which were comparable or superior to that of BAL30072. In vitro liver microsomal stability was further evaluated and the results manifested that Compounds 35, 46d and 54 were metabolically stable in human liver microsomes.

Ligand-Enabled Alkynylation of C(sp3)?H Bonds with Palladium(II) Catalysts

The palladium(II)-catalyzed β- and γ-alkynylation of amide C(sp3)?H bonds is enabled by pyridine-based ligands. This alkynylation reaction is compatible with substrates containing α-tertiary or α-quaternary carbon centers. The β-methylene C(sp