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(2S)-2-[[(1,1-Dimethylethoxy)carbonyl]amino]-4-pentynoic acid methyl ester, commonly known as Fmoc-L-homopropargylglycine methyl ester, is a chemical compound that serves as a versatile building block in the synthesis of peptide and protein conjugates. As a derivative of the amino acid glycine, it features a homopropargyl group and an Fmoc protecting group, which allows for selective deprotection and functionalization. The alkynyl functionality of this compound makes it particularly useful for click chemistry, a technique widely employed in bioconjugation. This makes it a valuable asset in various research fields, including drug development, chemical biology, and materials science.

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  • 71460-02-1 Structure
  • Basic information

    1. Product Name: (2S)-2-[[(1,1-Dimethylethoxy)carbonyl]amino]-4-pentynoic acid methyl ester
    2. 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
    3. CAS NO:71460-02-1
    4. Molecular Formula: C11H17NO4
    5. Molecular Weight: 227.25698
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 71460-02-1.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: N/A
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: N/A
    6. Refractive Index: N/A
    7. Storage Temp.: 2-8°C
    8. Solubility: N/A
    9. CAS DataBase Reference: (2S)-2-[[(1,1-Dimethylethoxy)carbonyl]amino]-4-pentynoic acid methyl ester(CAS DataBase Reference)
    10. NIST Chemistry Reference: (2S)-2-[[(1,1-Dimethylethoxy)carbonyl]amino]-4-pentynoic acid methyl ester(71460-02-1)
    11. EPA Substance Registry System: (2S)-2-[[(1,1-Dimethylethoxy)carbonyl]amino]-4-pentynoic acid methyl ester(71460-02-1)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 71460-02-1(Hazardous Substances Data)

71460-02-1 Usage

Uses

Used in Bioconjugation:
(2S)-2-[[(1,1-Dimethylethoxy)carbonyl]amino]-4-pentynoic acid methyl ester is used as a building block for the synthesis of diverse peptide and protein conjugates due to its homopropargyl group, which facilitates the formation of stable covalent bonds with other biomolecules.
Used in Click Chemistry:
In the field of chemical biology, (2S)-2-[[(1,1-Dimethylethoxy)carbonyl]amino]-4-pentynoic acid methyl ester is used as a reactant in click chemistry for the efficient and specific ligation of biomolecules, taking advantage of its alkynyl functionality to form stable triazole linkages.
Used in Drug Development:
(2S)-2-[[(1,1-Dimethylethoxy)carbonyl]amino]-4-pentynoic acid methyl ester is utilized as a key component in the design and synthesis of novel drug candidates, where its ability to be selectively deprotected and functionalized contributes to the creation of targeted therapeutic agents.
Used in Materials Science:
In the realm of materials science, (2S)-2-[[(1,1-Dimethylethoxy)carbonyl]amino]-4-pentynoic acid methyl ester is employed as a component in the development of biocompatible and functional materials, leveraging its chemical reactivity and versatility to create advanced material systems.
Used in Research Applications:
Across various research fields, (2S)-2-[[(1,1-Dimethylethoxy)carbonyl]amino]-4-pentynoic acid methyl ester is used as a research tool for exploring new chemical reactions and mechanisms, as well as for the development of innovative methodologies in organic synthesis and bioconjugation.

Check Digit Verification of cas no

The CAS Registry Mumber 71460-02-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,1,4,6 and 0 respectively; the second part has 2 digits, 0 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 71460-02:
(7*7)+(6*1)+(5*4)+(4*6)+(3*0)+(2*0)+(1*2)=101
101 % 10 = 1
So 71460-02-1 is a valid CAS Registry Number.

71460-02-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name (S)-N-Boc-α-propargylglycine methyl ester

1.2 Other means of identification

Product number -
Other names METHYL 2-[((1,1-DIMETHYLETHOXY)CARBONYL)AMINO]-4-PENTYNOATE

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:71460-02-1 SDS

71460-02-1Relevant articles and documents

6-SUBSTITUTED 3-FLUORO-2-PYRIDINALDOXIME, 3-FLUORO-2-PYRIDINE HYDROXAMIC ACID, AND 3-FLUORO-2-PYRIDINAMIDOXIME SCAFFOLDS

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Paragraph 0045; 0109; 0110, (2019/05/04)

The present invention relates to a compound of formula (I), as well as to a process for preparing the compounds of formula (I) by a chemoselective Sonogashira reaction. It also relates to a pharmaceutical composition comprising at least one compound of formula (I) and at least one pharmaceutically acceptable support. Finally, it relates to the use of such a compound as a medicine, preferably in the treatment of a nervous and/or respiratory failure due to intoxication with at least one organophosphorous nerve agent; in the treatment of neurological diseases such as Alzheimer's disease; and/or in the treatment of cancer; and/or for use as antiviral drug.

Stable cyclopropene-containing analogs of the amino acid neurotransmitter glutamate

Kumar, Pratik,Huang, Wei,Shukhman, David,Camarda, Frank M.,Laughlin, Scott T.

supporting information, p. 1476 - 1480 (2019/05/07)

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

Kou, Qunhuan,Wang, Ting,Zou, Feng,Zhang, Shuhua,Chen, Qian,Yang, Yushe

, p. 98 - 109 (2018/04/05)

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.

Sonogashira Reaction of Bromofluoropyridinaldoxime Nuclei: Convergent Synthesis of Functionalized 2- and 3-Fluoropyridine Scaffolds

Yerri, Jagadeesh,Baati, Rachid

supporting information, p. 4161 - 4165 (2018/08/21)

A chemoselective palladium catalyzed Sonogashira cross-coupling of bromofluoropyridinaldoxime with highly functionalized alkynes is presented. This reaction is fully compatible with unprotected sensitive aldoxime and affords representative underexplored new scaffolds. The process exhibits a broad scope of alkynes, dialkynes, and large functional group compatibility, including the use of non-radioactive isotopic reporter such as 15N labeled oxime and chiral substrates.

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

Fu, Haiyan,Shen, Peng-Xiang,He, Jian,Zhang, Fanglin,Li, Suhua,Wang, Peng,Liu, Tao,Yu, Jin-Quan

, p. 1873 - 1876 (2017/02/05)

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

Gold-Catalyzed Cycloisomerization of Alkyne-Containing Amino Acids: Controlled Tuning of C–N vs. C–O Reactivity

Medran, Noelia S.,Villalba, Matías,Mata, Ernesto G.,Testero, Sebastián A.

, p. 3757 - 3764 (2016/08/16)

Versatile alkyne-containing amino acids were used as ambident precursors in the divergent synthesis of alkylidenelactones and 1-pyrrolines. Two gold-catalyzed protocols were applied for selective intramolecular O- and N-cycloisomerization reactions.

BROAD SPECTRUM ANTIBIOTICS

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Page/Page column 194, (2013/02/27)

Provided herein are antibacterial compounds, wherein the compounds in some embodiments have broad spectrum bioactivity. The compounds provided herein can in other embodiments overcome the resistance conferred by single amino acid mutations at defined posi

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

Sogawa, Hiromitsu,Shiotsuki, Masashi,Sanda, Fumio

, p. 2008 - 2018 (2012/07/13)

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.

1,2,3-Triazolyl amino acids as AMPA receptor ligands

Stanley,Pedersen, D. Sejer,Nielsen,Kvist,Mathiesen,Br?uner-Osborne,Taylor,Abell

supporting information; experimental part, p. 7512 - 7515 (2011/03/17)

The central nervous system glutamate receptors are an important target for drug discovery. Herein we report initial investigations into the synthesis and glutamate receptor activity of 1,2,3-triazolyl amino acids. Two compounds were found to be selective

Synthesis of optically active α-(allenyl)-and a-substituted-α- (allenyl)glycines

Takuya Okada,Oda, Naoko,Suzuki, Hiroyuki,Sakaguchi, Kazuhiko,Ohfune, Yasufumi

supporting information; experimental part, p. 3765 - 3768 (2010/08/22)

The synthesis of various types of optically active α-(allenylsilane- containing)glycines via a chiralitytransferring ester-enolate Claisen rearrangement of α-acyloxy-a-alkynylsilanes is described. The conversion of the rearranged products into the optically active silicon-free α-(allenyl)-and α-substituted-α-(allenyl)glycines was achieved by the removal of the Me2PhSi-or TMS group from the allene terminus.

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