91000-69-0

Basic information

• Product Name: FMOC-L-Arginine
• Synonyms: FMOC-L-ARGININE extrapure;(9-fluorenylmethoxycarbonyl)-L-arginine-OH;Nα-Fmoc-L-arginine, Nα-(9-Fluorenylmethoxycarbonyl)-L-arginine;(2S)-5-(Diaminomethylideneazaniumyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)pentanoate;L-Arginine, N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-;NALPHA-FMOC-L-ARGININE, 99+%;Nα-(9-Fluorenylmethyloxycarbonyl)-L-arginine ,98%;(S)-2-((((9H-fluoren-9-yl)Methoxy)carbonyl)aMino)-5-guanidinopentanoic acid
• CAS NO: 91000-69-0
• Molecular Formula: C₂₁H₂₄N₄O₄
• Molecular Weight: 396.44
• Product Categories: Amino Acids;Arginine [Arg, R];Fmoc-Amino Acids and Derivatives;Fmoc-Amino acid series;Others;Amino Acid Derivatives
• Mol File: 91000-69-0.mol
• Article Data: 8

Chemical Properties

• Melting Point: 145-150 °C(lit.)
• Boiling Point: 520.14°C (rough estimate)
• Appearance: Off-white/Powder
• Density: 1.2722 (rough estimate)
• Refractive Index: 1.6620 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Aqueous Acid (Slightly), Chloroform (Slightly), Dimethylformamide (Slightly)
• PKA: 3.81±0.21(Predicted)
• Sensitive: Moisture Sensitive
• BRN: 4828015
• CAS DataBase Reference: FMOC-L-Arginine(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-L-Arginine(91000-69-0)
• EPA Substance Registry System: FMOC-L-Arginine(91000-69-0)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 21
• Hazardous Substances Data: 91000-69-0(Hazardous Substances Data)

Usage

Description

FMOC-L-Arginine, also known as Nα-Fmoc-L-arginine, is an N-Fmoc-protected form of L-Arginine, a conditionally essential amino acid for humans and adult mammals. It is required during certain developmental stages in life, such as pregnancy, when the body's production is insufficient to meet its needs. Additionally, L-Arginine helps prevent blood toxicity from intravenous amino acid administration in humans. FMOC-L-Arginine is characterized by its white to light yellow crystal powder appearance.

Uses

Used in Pharmaceutical Industry:
FMOC-L-Arginine is used as a building block in the synthesis of various pharmaceutical compounds. The N-Fmoc protection group allows for selective deprotection and coupling reactions, facilitating the creation of complex peptide structures.
Used in Research and Development:
FMOC-L-Arginine serves as a valuable research tool in the study of amino acid chemistry, peptide synthesis, and related biological processes. Its protected form enables researchers to explore the properties and interactions of L-Arginine in a controlled manner.
Used in Nutritional Supplements:
FMOC-L-Arginine can be utilized in the development of nutritional supplements to support the conditional essential amino acid requirements of humans and adult mammals, particularly during specific developmental stages such as pregnancy.
Used in Drug Delivery Systems:
FMOC-L-Arginine can be incorporated into drug delivery systems to enhance the bioavailability and therapeutic efficacy of L-Arginine. This may involve the use of nanoparticles or other carriers to improve the delivery and targeting of L-Arginine to specific tissues or cells.

InChI:InChI=1/C21H24N4O4/c22-20(23)24-11-5-10-18(19(26)27)25-21(28)29-12-17-15-8-3-1-6-13(15)14-7-2-4-9-16(14)17/h1-4,6-9,17-18H,5,10-12H2,(H,25,28)(H,26,27)(H4,22,23,24)/t18-/m1/s1

Upstream product

• 98930-01-9 Nα-(9-fluorenylmethoxycarbonyl)-Nγ-(4-methoxy-2,3,6-trimethylbenzenesulphonyl)-L-arginine 
• 116220-89-4 N^α-9-Fluorenylmethyloxycarbonyl-N^G-2,4,6-triisopropylbenzenesulphonyl-L-arginine 
• 162611-62-3 N^α-9-fluorenylmethyloxycarbonyl-N^G-biphenyl-4-sulphonyl-L-arginine 
• 74-79-3 L-arginine 
• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 3006-96-0 3-hydroxymethyl-benzoic acid 
• 187618-60-6 Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine 
• 1202179-48-3 Fmoc-Arg-HMBA-Arg₆-OH 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 160252-91-5 N^α-9-Fluorenylmethyloxycarbonyl-N^G-4-methoxy-3,5-di-tert-butylbenzenesulphonyl-L-arginine 

Downstream Products

• 58-82-2 bradykinin 
• 191936-91-1 Tyr-Gly-Arg-Lys-Lys-Arg-Arg-Gln-Arg-Arg-Arg 
• 1035896-23-1 C₄₆H₈₂N₁₈O₁₅ 

Relevant articles and documents

New TFA-free cleavage and final deprotection in Fmoc solid-phase peptide synthesis: Dilute HCl in fluoro alcohol

A novel method for cleaving from resin and removing acid-labile protecting groups for the Fmoc solid-phase peptide synthesis is described. 0.1 N HCl in hexafluoroisopropanol or trifluoroethanol cleanly and rapidly removes the tert-butyl ester and ether, Boc, trityl, and Pbf groups and cleaves the common resin linkers: Wang, HMPA, Rink amide, and PAL. Addition of just 5-10% of a hydrogen-bonding solvent considerably retards or even fully inhibits the reaction. However, a non-hydrogen-bonding solvent is tolerated.

Synthesis of an arginine tagged [Cys155-Arg180] fragment of NY-ESO-1: elimination of an undesired by-product using 'In house' resins

During the solid-phase synthesis of a peptide fragment derived from the cancer protein NY-ESO-1 incorporating a solubilising arginine tag, a significant by-product was obtained that lacked the arginine tag. The formation of this by-product (and others) wa

Facile solid-phase synthesis of sulfated tyrosine-containing peptides: Total synthesis of human big gastrin-II and cholecystokinin (CCK)-39

Chemical synthesis of tyrosine O-sulfated peptides is still a laborious task for peptide chemists because of the intrinsic acid-lability of the sulfate moiety. An efficient cleavage/deprotection procedure without loss of the sulfate is the critical difficulty remaining to be solved for fluoren-9-ylmethoxycarbonyl (Fmoc)-based solid-phase synthesis of sulfated peptides. To overcome the difficulty, TFA-mediated solvolysis rates of a tyrosine O-sulfate [Tyr(SO3H)] residue and two protecting groups, tBu for the hydroxyl group of Ser and 2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl (Pbf) for the guanidino group of Arg, were examined in detail. The desulfation obeyed first-order kinetics with a large entropy (59.6 J·K-1·mol-1) and enthalpy (110.5 kJ·mol-1) of activation. These values substantiated that the desulfation rate of the rigidly solvated Tyr(SO3H) residue was strongly temperature-dependent. By contrast, the SN1-type deprotections were less temperature-dependent and proceeded smoothly in TFA of a high ionizing power. Based on the large rate difference between the desulfation and the SN1-type deprotections in cold TFA, an efficient deprotection protocol for the sulfated peptides was developed. Our synthetic strategy for Tyr(SO3H)containing peptides with this effective deprotection protocol is as follows: (i) a sulfated peptide chain is directly constructed on 2-chlorotrityl resin with Fmoc-based solid-phase chemistry using Fmoc-Tyr(SO3Na)-OH as a building block; (ii) the protected peptide-resin is treated with 90% aqueous TFA at 0 °C for an appropriate period of time for the cleavage and deprotection. Human cholecystokinin (CCK)-12, mini gastrin-II (14 residues), and little gastrin-II (17 residues) were synthesized with this method in 26-38% yields without any difficulties. This method was further applied to the stepwise synthesis of human big gastrin-II (34 residues), CCK-33 and -39. Despite the prolonged acid treatment (15-18 h at 0 °C), the ratios of the desulfated peptides were less than 15%, and the pure sulfated peptides were obtained in around 10% yields.