61172-66-5

Basic information

• Product Name: N-Boc-2-propargyl-glycine
• Synonyms: 2-(Boc-amino)-4-pentynoic acid;N-Boc-2-propargyl-glycine;2-((tert-butoxycarbonyl)aMino)pent-4-ynoic acid;2-(tert-butoxycarbonyl)pent-4-ynoic acid;4-Pentynoic acid, 2-[[(1,1-dimethylethoxy)carbonyl]amino]-;Boc-RS-2-Propynylglycine
• CAS NO: 61172-66-5
• Molecular Formula: C₁₀H₁₅NO₄
• Molecular Weight: 213.2304
• EINECS: -0
• Mol File: 61172-66-5.mol

Chemical Properties

• Appearance: /
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: N-Boc-2-propargyl-glycine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Boc-2-propargyl-glycine(61172-66-5)
• EPA Substance Registry System: N-Boc-2-propargyl-glycine(61172-66-5)

Safety Data

• Hazardous Substances Data: 61172-66-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
N-Boc-2-propargyl-glycine is used as a building block for the synthesis of various biologically active molecules and pharmaceuticals. Its presence of a Boc protecting group and a propargyl functional group allows for the creation of a wide range of compounds with potential therapeutic applications.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, N-Boc-2-propargyl-glycine is utilized as a key intermediate in the development of new drugs. Its unique structure and functional groups enable the design and synthesis of innovative pharmaceutical agents with improved efficacy and selectivity.
Used in Drug Discovery:
N-Boc-2-propargyl-glycine plays a significant role in drug discovery, where it is employed to explore and identify novel therapeutic agents. Its potential applications in this field contribute to the ongoing efforts to develop new treatments for various diseases and conditions.
Used in Pharmaceutical Research:
As a compound with a significant role in the advancement of chemical and pharmaceutical research, N-Boc-2-propargyl-glycine is used to investigate new synthetic routes, reaction mechanisms, and the properties of newly synthesized compounds. This research helps to expand the understanding of chemical processes and contributes to the development of more effective and safer pharmaceuticals.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 23235-01-0 (R)-2-aminopent-4-ynoic acid 
• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 23235-01-0 L-Propargylglycine 

Relevant articles and documents

D-ALA-D-ALA-BASED DIPEPTIDES AS TOOLS FOR IMAGING PEPTIDOGLYCAN BIOSYNTHESIS

Disclosed herein are compositions for assessing peptidoglycan biosynthesis in bacteria using modified dipeptides containing a bioorthogonal tag and applying novel post-labeling methods to label the bioorthogonal tag. The resultant, labeled peptidoglycan structures are amenable for identifying bacteria by microscopic visualization.

α-Propargyl amino acid-derived optically active novel substituted polyacetylenes: Synthesis, secondary structures, and responsiveness to ions

Novel optically active substituted acetylenes HCi￡ CCH 2CR1(CO2CH3)NHR2 [(S)-/(R)-1: R1 = H, R2 = Boc, (S)-2: R1 = CH3, R2 = Boc, (S)-3: R1 = H, R2 = Fmoc, (S)-4: R1 = CH3, R2 = Fmoc (Boc = tert-butoxycarbonyl, Fmoc = 9-fluorenylmethoxycarbonyl)] were synthesized from α-propargylglycine and α-propargylalanine, and polymerized with a rhodium catalyst to provide the polymers with number-average molecular weights of 2400-38,900 in good yields. Polarimetric, circular dichroism (CD), and UV-vis spectroscopic analyses indicated that poly[(S)-1], poly[(R)-1], and poly[(S)-4] formed predominantly one-handed helical structures both in polar and nonpolar solvents. Poly[(S)-1a] carrying unprotected carboxy groups was obtained by alkaline hydrolysis of poly[(S)-1], and poly[(S)-4b] carrying unprotected amino groups was obtained by removal of Fmoc groups of poly[(S)-4] using piperidine. Poly[(S)-1a] and poly[(S)-4b] also exhibited clear CD signals, which were different from those of the precursors, poly[(S)-1] and poly[(S)-4]. The solution-state IR measurement revealed the presence of intramolecular hydrogen bonding between the carbamate groups of poly[(S)-1] and poly[(S)-1a]. The plus CD signal of poly[(S)-1a] turned into minus one on addition of alkali hydroxides and tetrabutylammonium fluoride, accompanying the red-shift of λmax. The degree of λmax shift became large as the size of cation of the additive.

N6-(2-(R)-propargylglycyl)lysine as a clickable pyrrolysine mimic

Clickable copycat! Readily available dipeptide d-Pra-ε-Lys is identified using a modified fluorescence protein assay as a highly efficient clickable pyrrolysine mimic. It is shown to incorporate into calmodulin in high yield to provide a handle for labeling with anazide-containing coumarin.

Palladium-Catalyzed Cyclization Reactions of Acetylene-Containing Amino Acids

Enantiomerically pure acetylene-containing α-amino acids were used as versatile starting materials for the synthesis of a variety of heterocycles via Pd-mediated cyclization reactions. Depending on the protecting group strategy, both the carboxylate and the amine function of the amino acids could participate in the cyclizations, thus giving rise to oxygen heterocycles (α-aminolactones) and nitrogen heterocycles (cyclic α-amino acid derivatives), respectively. Beside the straightforward cyclization, cyclization/cross-coupling reactions were also successfully carried out to provide the corresponding substituted cyclic amino acid derivatives.

Synthesis, properties and crystal structure of the tripeptide boc-L-prolyl-L-propargylglycyl-glycine methylester

Propargylglycine, as a powerful inhibitor of microbial growth, was built into a protected tripeptide with the sequence Pro-Pra-Gly. The peptide was employed to study its effects on the activity of prolyl 4-hydroxylase and the collagen biosynthesis. The Boc-protected tripeptide methylester was identified by mass spectrometry and NMR spectroscopy and its crystal structure was established by X-ray diffraction analysis.