71989-31-6

Basic information

• Product Name: FMOC-L-Proline
• Synonyms: N-9-FLUORENYLMETHYLOXYCARBONYL-L-PROLINE;N-(9-FLUOROENYLMETHOXYCARBONYL)-L-SERINE;N-(9-FLUORENYLMETHOXYCARBONYL)-L-PROLINE;N-(9-FLUORENYLMETHOXYCARBONYL)-L-PYRROLIDINE-2-CARBOXYLIC ACID;N-ALPHA-FMOC-L-PROLINE;9-FLUORENYLMETHOXYCARBONYL-L-PROLINE;FMOC-L-PRO-OH;FMOC-L-PRO-OH H2O
• CAS NO: 71989-31-6
• Molecular Formula: C₂₀H₁₉NO₄
• Molecular Weight: 337.37
• EINECS: 276-259-0
• Product Categories: Protected Amino Acids;Fluorenes, Flurenones;Amino Acids;Proline [Pro, P];Fmoc-Amino Acids and Derivatives;Amino Acids (N-Protected);Biochemistry;Fmoc-Amino Acids;Fmoc-Amino acid series
• Mol File: 71989-31-6.mol

Chemical Properties

• Melting Point: 117-118 °C(lit.)
• Boiling Point: 473.68°C (rough estimate)
• Flash Point: 285.6 °C
• Appearance: white to light yellow crystal powder
• Density: 1.2486 (rough estimate)
• Vapor Pressure: 7.19E-13mmHg at 25°C
• Refractive Index: -32.5 ° (C=1, DMF)
• Storage Temp.: 2-8°C
• Solubility: Soluble in methanol. (almost transparency.)
• PKA: 3.95±0.20(Predicted)
• BRN: 3596735
• CAS DataBase Reference: FMOC-L-Proline(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-L-Proline(71989-31-6)
• EPA Substance Registry System: FMOC-L-Proline(71989-31-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25
• WGK Germany: 3
• Hazardous Substances Data: 71989-31-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Fmoc-L-Proline is used as a building block for the synthesis of collagen-based drugs and treatments, targeting conditions related to connective tissue repair and wound healing. Its role in collagen production makes it a valuable component in the development of therapeutic agents for various medical applications.
Used in Nutritional Supplements:
Fmoc-L-Proline is used as an ingredient in nutritional supplements designed to support collagen production and overall skin, joint, and connective tissue health. Its presence in these supplements helps promote the body's natural healing processes and maintain the integrity of tissues.
Used in Cosmetic Industry:
Fmoc-L-Proline is used as an active ingredient in anti-aging and skin care products, where it contributes to collagen synthesis and helps improve skin elasticity, hydration, and overall appearance. Its role in maintaining healthy skin makes it a sought-after component in various cosmetic formulations.
Used in Research and Development:
Fmoc-L-Proline is utilized as a research tool in the development of new drugs, therapies, and treatments targeting connective tissue disorders, wound healing, and tissue regeneration. Its unique properties and role in collagen synthesis make it an essential component in the advancement of medical and cosmetic products.

InChI:InChI=1/C20H19NO4/c22-19(23)18-10-5-11-21(18)20(24)25-12-17-15-8-3-1-6-13(15)14-7-2-4-9-16(14)17/h1-4,6-9,17-18H,5,10-12H2,(H,22,23)/p-1/t18-/m0/s1

Upstream product

• 24324-17-2 9-Fluorenylmethanol 
• 147-85-3 L-proline 
• 5269-62-5 L-proline trimethylsilyl ester 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 851713-91-2 N-(9-fluorenylmethoxycarbonyl)proline 1,1-dimethylallyl ester 
• 474316-88-6 Fmoc-Pro-NHNHPh 
• 100821-63-4 1,2,2,2-Tetrachloroethyl 9-fluorenylmethyl carbonate 
• 344-25-2 D-Prolin 
• 88744-04-1 (9-fluorenyl)methyl pentafluorophenyl carbonate 
• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 802918-70-3 N-(9-fluorenylmethoxycarbonyl)-proline allyl ester 
• 7776-34-3 L-proline hydrochloride 
• 1307875-26-8 tert-butyl N-(methoxycarbonyl)-L-prolinate 
• 1298116-72-9 1-((9H-fluoren-9-yl)methyl) 2-benzyl (S)-pyrrolidine-1,2-dicarboxylate 

Downstream Products

• 164861-48-7 Z-L-Phe-L-Val-L-Pro-NH₂ 
• 83871-06-1 N-benzyloxycarbonyl-L-phenylalanyl-L-prolinamide 
• 95501-78-3 N-Benzyloxycarbonyl-L-valyl-L-prolyl-L-valinal 
• 29635-99-2 hexahydro-2-phenyl-3-thioxopyrrolo[1,2-c]imidazol-1-one 

Relevant articles and documents

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Fmoc-OPhth, the reagent of Fmoc protection

Fmoc-OSu has been widely used for Fmoc protection of amino groups, especially amino acids, in solid phase peptide synthesis. However, it has been recognized that Fmoc-βAla-OH is formed as a by-product via the Lossen rearrangement during the reaction. Since we reconfirmed the formation of Fmoc-βAla-OH during the preparation of Fmoc-AA-OH by Fmoc-OSu, Fmoc-OPhth was designed and synthesized as a new Fmoc reagent to avoid the formation of Fmoc-βAla-OH. Furthermore, Fmoc protection by Fmoc-OPhth and Fmoc-SPPS were evaluated. The various Fmoc-amino acids prepared by Fmoc-OPhth were carried out in good yields and these are applicable in Fmoc-SPPS.

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As an alternative approach to the graft modification of polymers to fabricate polymer-supported chiral organocatalysts in a bottom-up fashion, L-prolinamide functionalized polymers were prepared by general solution homopolymerization or copolymerization of L-proline functionalized styrene monomer in the presence of 1,4-divinylbenzene as the crosslinking agent. The catalytic performance of the as-prepared heterogeneous catalysts towards the direct enantioselective aldol reaction of ketones with a series of aromatic aldehydes was explored. Our findings indicate that the as-prepared heterogeneous catalysts can afford relevant aldol addition products with good yields (up to 96%), high diastereoselectivities (up to 8:92 dr) and excellent enantiomeric excess (up to 96%); they also exhibit good recyclability, retaining high yield and rate as well as good selectivity after several cycles.

Caged xanthones: Potent inhibitors of global predominant MRSA USA300

Total of 22 caged xanthones were subjected to susceptibility testing of global epidemic MRSA USA300. Natural morellic acid showed the strongest potency (MIC of 12.5 μM). However, its potent toxicity diminishes MRSA therapeutic potential. We synthetically modified natural morellic acid to yield 13 derivatives (3a-3m). Synthetically modified 3b retained strong potency in MRSA growth inhibition, yet the toxicity was 20-fold less than natural morellic acid, permitting the possibility of using caged xanthones for MRSA therapeutic.

THERAPEUTICALLY ACTIVE COMPOUNDS AND THEIR METHODS OF USE

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The scope of MgI2 as a valuable tool for quantitative and mild chemoselective cleavage of protecting groups is described here. This novel synthetic approach expands the use of protecting groups, widens the concept of orthogonality in synthetic processes, and offers a facile opportunity to release compounds from solid supports. Amazing MgI2: Protecting groups have had a tremendous positive impact on the art of biomolecule synthesis. In a context in which the use of attractive protecting groups is often limited by harsh deprotection conditions and low chemoselective flexibility, MgI2 offers, by the execution of a very simple protocol, a fresh vision with extensive perspectives.

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Octaarginine has been described as a molecular transporter. We report a useful synthesis of orthogonally protected l-octaarginine by using a method based on a microencapsulated palladium catalyst. Known palladium-based methods for allyl ester deprotection have been modified to facilitate purification of the unprotected intermediates. This improvement in the purification step has also been tested with a variety of allyl α-amino esters and allyl α,β-unsaturated esters.

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The study describes a new "one-pot" route to the synthesis of N-9-fluorenylmethyloxycarbonyl (Fmoc) α-amino diazoketones. The procedure was tested on a series of commercially available free or side-chain protected α-amino acids employed as precursors. The conversion into the title compounds was achieved by masking and activating the α-amino acids with a single reagent, namely, 9-fluorenylmethyl chloroformate (Fmoc-Cl). The resulting N-protected mixed anhydrides were reacted with diazomethane to lead to the α-amino diazoketones, which were isolated by flash column chromatography in very good to excellent overall yields. The versatility of the procedure was verified on lipophilic α-amino acids and further demonstrated by the preparation of N-Fmoc-α-amino diazoketones also from α-amino acids containing side-chain masking groups, which are orthogonal to the Fmoc one. The results confirmed that tert-butyloxycarbonyl (Boc), tert-butyl (tBu), and 2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl (Pbf), three acid-labile protecting groups mostly adopted in the solution and solid-phase peptide synthesis, are compatible to the adopted reaction conditions. In all cases, the formation of the corresponding C-methyl ester of the starting amino acid was not observed. Moreover, the proposed method respects the chirality of the starting α-amino acids. No racemization occurred when the procedure was applied to the synthesis of the respective N-Fmoc-protected α-amino diazoketones from l-isoleucine and l-threonine and to the preparation of a diastereomeric pair of N-Fmoc-protected dipeptidyl diazoketones.