Fmoc-L-Propargylglycine

Base Information

• Chemical Name: Fmoc-L-Propargylglycine
• CAS No.: 198561-07-8
• Molecular Formula: C20H17NO4
• Molecular Weight: 335.359
• Hs Code.: 29242990
• DSSTox Substance ID: DTXSID80370319
• Nikkaji Number: J2.537.041D
• Wikidata: Q72478845
• Mol file: 198561-07-8.mol

Synonyms:Fmoc-L-Propargylglycine;198561-07-8;Fmoc-Pra-OH;(S)-2-(Fmoc-amino)-4-pentynoic acid;Fmoc-propargyl-Gly-OH;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)pent-4-ynoic acid;4-Pentynoic acid, 2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-, (2S)-;(2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)pent-4-ynoic acid;(S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)pent-4-ynoic acid;MFCD01075095;Fmoc-L-2-propargylglycine;Fmoc-Gly(propargyl)-OH;Fmoc-L-Pra-OH;N-Fmoc-L-propargylglycine;N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-propargylglycine;Fmoc-alpha-Propargyl-Gly-OH;Fmoc-(S)-2-Propargylglycine;Fmoc-Propargyl-Gly-OH;SCHEMBL119866;DTXSID80370319;DJGMNCKHNMRKFM-SFHVURJKSA-N;(S)-N-FMOC-PROPARGYLGLYCINE;(2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}pent-4-ynoic acid;LT0116;AKOS015948708;AC-9949;AM82637;CS-W011926;GS-6245;HY-W011210;F0926;Fmoc-propargyl-Gly-OH, >=98.0% (HPLC);EN300-332804;F12334;A814014;J-300362;N-FLUORENEMETHOXYCARBONYL-L-PROPARGYL GLYCINE;S-198561-07-8;N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-PROPARGYLGLYCINE;(2S)-2-{[(9H-Fluoren-9-ylmethoxy)carbonyl]amino}-4-pentynoic acid;(S)-N-(9-FLUORENYLMETHOXYCARBONYL)-2-AMINO-4-PENTYNOIC ACID;N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-L-PROPARGYLGLYCINE;N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-(S)-2-AMINO-4-PENTYNOIC ACID

Chemical Property of Fmoc-L-Propargylglycine

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 3.84E-14mmHg at 25°C
• Melting Point: 175 °C
• Refractive Index: 1.618
• Boiling Point: 576.7 °C at 760 mmHg
• PKA: 3.42±0.10(Predicted)
• Flash Point: 302.6 °C
• PSA: 75.63000
• Density: 1.292 g/cm³
• LogP: 3.39250
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Sparingly)
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 335.11575802
• Heavy Atom Count: 25
• Complexity: 529

Purity/Quality:

98%,99%, ^*data from raw suppliers

FMoc-L-Propargylglycine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 24/25-25-24

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C#CCC(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Isomeric SMILES: C#CC[C@@H](C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Uses: Fmoc-propargyl-Gly-OH is an Fmoc protected glycine derivative useful for solid phase peptide synthesis techniques. This compound could be useful as an unusual amino acid analog to aid in the deconvolution of protein structure and function. N-Fmoc-L-propargylglycine is a non-natural amino acids used for the triazole cross-link.

Technology Process of Fmoc-L-Propargylglycine

There total 5 articles about Fmoc-L-Propargylglycine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

tert-butyl–(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)pent-4-ynoate (857335-00-3) → Fmoc-L-propargyl-Gly-OH (198561-07-8)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 15h;

DOI:10.1021/ja303831a

Reference yield: 65.0%

(2S)-2-amino-4-pentynoic acid (23235-01-0) + 9-fluorenylmethyl N-succinimidyl carbonate (102774-86-7) → Fmoc-L-propargyl-Gly-OH (198561-07-8)

Guidance literature:

With sodium hydrogencarbonate; In tetrahydrofuran; water; at 20 ℃;

DOI:10.1039/c0cc04795c

Reference yield: 63.0%

(2S)-2-amino-4-pentynoic acid (23235-01-0) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → Fmoc-L-propargyl-Gly-OH (198561-07-8)

Guidance literature:

With potassium carbonate; In 1,4-dioxane; water; at 0 ℃; for 0.5h; Inert atmosphere;

DOI:10.1055/s-0032-1317445 DOI:10.1055/s-0032-1317445

upstream raw materials:

tert-butyl–(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)pent-4-ynoate

(2S)-2-amino-4-pentynoic acid

9-fluorenylmethyl N-succinimidyl carbonate

2-amino-pent-4-ynoic acid tert-butyl ester

Downstream raw materials:

Nα-Ac-Lys-Gly-Pra-Ser-Ile-Gln-Nle(ε-N3)-Leu-Arg-NH2

Nα-Ac-Lys-Gly-Pra-Ser-Ile-Gln-Nva(δ-N3)-Leu-Arg-NH2

Nα-Ac-Lys-Gly-Nva(δ-N3)-Ser-Ile-Gln-Pra-Leu-Arg-NH2

(S)-3-{[((9H-fluoren-9-yl)methoxy)carbonyl]amino}hex-5-ynoic acid

Refernces

• 1、 Einsiedler, Manuel,Jamieson, Cooper S.,Maskeri, Mark A.,Houk, Kendall N.,Gulder, Tobias A. M.. "Fungal Dioxygenase AsqJ Is Promiscuous and Bimodal: Substrate-Directed Formation of Quinolones versus Quinazolinones". supporting information. p. 8297 - 8302. Retrieved 2021/03/01.
• 2、 Sogawa, Hiromitsu,Shiotsuki, Masashi,Sanda, Fumio. "α-Propargyl amino acid-derived optically active novel substituted polyacetylenes: Synthesis, secondary structures, and responsiveness to ions". experimental part. p. 2008 - 2018. Retrieved 2012/07/13.