198561-07-8

Basic information

• Product Name: FMOC-L-PROPARGYLGLYCINE
• Synonyms: (S)-N-(9-FLUORENYLMETHOXYCARBONYL)-2-AMINO-4-PENTYNOIC ACID;(S)-N-FMOC-PROPARGYLGLYCINE;(S)-2-(FMOC-AMINO)-4-PENTYNOIC ACID;RARECHEM BK PT 0257;N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-PROPARGYLGLYCINE;N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-(S)-2-AMINO-4-PENTYNOIC ACID;N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-L-PROPARGYLGLYCINE;FMOC-PRA-OH
• CAS NO: 198561-07-8
• Molecular Formula: C₂₀H₁₇NO₄
• Molecular Weight: 335.35
• Product Categories: Amino Acids;Unusual amino acids;Amino Acid Derivatives
• Mol File: 198561-07-8.mol
• Article Data: 8

Chemical Properties

• Melting Point: 175 °C
• Boiling Point: 472°C (rough estimate)
• Flash Point: 302.6 °C
• Appearance: white powder
• Density: 1.2712 (rough estimate)
• Vapor Pressure: 3.84E-14mmHg at 25°C
• Refractive Index: 1.5600 (estimate)
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Sparingly)
• PKA: 3.42±0.10(Predicted)
• CAS DataBase Reference: FMOC-L-PROPARGYLGLYCINE(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-L-PROPARGYLGLYCINE(198561-07-8)
• EPA Substance Registry System: FMOC-L-PROPARGYLGLYCINE(198561-07-8)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 24/25-25-24
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 198561-07-8(Hazardous Substances Data)

Usage

Description

FMOC-L-PROPARGYLGLYCINE, also known as Fmoc-propargyl-Gly-OH, is an Fmoc protected glycine derivative that is primarily used in solid phase peptide synthesis techniques. It is a white powder and serves as an unusual amino acid analog, which can be beneficial in the deconvolution of protein structure and function. The compound is also used for the formation of triazole cross-links through N-Fmoc-L-propargylglycine, a non-natural amino acid.

Uses

Used in Pharmaceutical Industry:
FMOC-L-PROPARGYLGLYCINE is used as a building block for the synthesis of peptides and proteins, aiding in the development of new drugs and therapies. Its role in solid phase peptide synthesis allows for the creation of complex peptide structures, which can be crucial in the design and synthesis of novel pharmaceutical compounds.
Used in Research and Development:
FMOC-L-PROPARGYLGLYCINE is used as a research tool for studying protein structure and function. As an unusual amino acid analog, it can be incorporated into proteins to investigate their structural and functional properties, providing valuable insights into protein-protein interactions and other biological processes.
Used in Chemical Synthesis:
FMOC-L-PROPARGYLGLYCINE is used as a reagent in the synthesis of various chemical compounds, particularly those involving the formation of triazole cross-links. This application is important in the development of new materials and compounds with specific properties and functions.

InChI:InChI=1/C20H17NO4/c1-2-7-18(19(22)23)21-20(24)25-12-17-15-10-5-3-8-13(15)14-9-4-6-11-16(14)17/h1,3-6,8-11,17-18H,7,12H2,(H,21,24)(H,22,23)/t18-/m1/s1

Upstream product

• 857335-00-3 tert-butyl–(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)pent-4-ynoate 
• 71460-15-6 2-amino-pent-4-ynoic acid tert-butyl ester 
• 326667-54-3 tert-butyl (S)-2-[(diphenylmethylene)amino]pent-4-ynoate 
• 23235-01-0 (2S)-2-amino-4-pentynoic acid 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 102774-86-7 9-fluorenylmethyl N-succinimidyl carbonate 

Downstream Products

• 1203948-45-1 (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(2-tosylisoindolin-5-yl)propanoic acid, 
• 1203948-41-7 (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4,7-dimethyl-2-tosylisoindolin-5-yl)propanoic acid, 
• 1134204-68-4 Fmoc-Trp-Pra-Pra-Trp-NHBn 
• 1134204-66-2 Fmoc-Pra-Trp-NHBn 
• 1217669-02-7 (S)-3-{[((9H-fluoren-9-yl)methoxy)carbonyl]amino}hex-5-ynoic acid 
• 1584149-65-4 C₂₄H₃₇N₇O₆ 
• 1584149-71-2 C₃₀H₄₃N₇O₁₀ 
• 1612162-71-6 C₅₄H₇₅N₁₂O₂₂P₃S 
• 1217266-28-8 Nα-Ac-Lys-Gly-Nva(δ-N3)-Ser-Ile-Gln-Pra-Leu-Arg-NH2 
• 1217266-30-2 Nα-Ac-Lys-Gly-Pra-Ser-Ile-Gln-Nva(δ-N3)-Leu-Arg-NH2 
• 1217266-32-4 Nα-Ac-Lys-Gly-Pra-Ser-Ile-Gln-Nle(ε-N3)-Leu-Arg-NH2 
• 1134204-65-1 Fmoc-Pra-Gly-OBn 

Relevant articles and documents

Design, synthesis and functional analysis of dansylated polytheonamide mimic: An artificial peptide ion channel

We report herein the design, total synthesis, and functional analysis of a novel artificial ion channel molecule, designated as dansylated polytheonamide mimic (3). The channel 3 was designed based on an exceptionally potent cytotoxin, polytheonamide B (1

pDobz/pDobb protected diaminodiacid as a novel building block for peptide disulfide-bond mimic synthesis

The diaminodiacid strategy has been widely studied in the chemical synthesis of peptide disulfide bond mimics. Diaminodiacid building blocks, which are key intermediates, are currently under the spotlight. However, one technical bottleneck inherent in existing building blocks is the contamination problem caused by the heavy metal reagents during the deprotection process, which makes the peptides less suitable for pharmaceutical use. Herein, we describe the successful development of a p-dihydroxyborylbenzyloxycarbonyl pinacol ester (pDobz)- and p-dihydroxyborylbenzyl pinacol ester (pDobb)-based novel diaminodiacid building block that can be easily deprotected via mild treatment with amine oxide. Its efficiency and practicability were also confirmed by the total synthesis of contryphan-Vn disulfide bond mimic. The results suggested that this novel diaminodiacid building block has satisfactory Fmoc SPPS compatibility, yet only required a facile, rapid, and metal-free deprotection process. We believe this novel diaminodiacid building block could promote further development of the diaminodiacid strategy.

Azide- and alkyne-functionalised α- And β3-amino acids

The synthesis and full characterisation of bifunctional β3-amino acids that have side chains functionalised with terminal azides (S)-4 and (R)-4 or acetylenes 5 and 6 is reported for the first time. The building blocks incorporate a turn-inducing β3-segment and a side chain that can be functionalised further, for example, through copper-catalysed Huisgen cycloaddition. Moreover, the corresponding α-amino acids 1 and 3 have been synthesised and characterised. All amino acid building blocks were of high optical purity as demonstrated by derivatisation and subsequent NMR analysis. Georg Thieme Verlag KG Stuttgart · New York.