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
• Article Data: 29

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

Description

Fmoc-L-Proline, also known as N-Fmoc protected L-Proline, is an amino acid that serves as a precursor (along with vitamin C) for collagen. Collagen is a crucial component in the structure of various connective tissues such as tendons, ligaments, arteries, veins, and muscles. Fmoc-L-Proline plays a significant role in wound healing and tissue repair.

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

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

Downstream Products

• 71989-32-7 Fmoc-Pro-ONp 
• 125281-38-1 Fmoc-L-proline pentafluorophenyl ester 
• 127492-89-1 Ava-Phe-Phe-Pro-Leu-Met-NH₂ 
• 125281-19-8 O^1,4-(β-D-Glucopyranosyl)-4>-morphiceptin 
• 125281-19-8 O^1,4-(β-D-Galactopyranosyl)-4>-morphiceptin 
• 119138-21-5 Pyr-Thr(tBu)-Ser(tBu)-Phe-Thr(tBu)-Pro-OH 
• 160681-96-9 2-<4-(FMOC-L-prolyl-amino)phenyl>-1,3-dithiolane 
• 136631-85-1 phenacyl (9-fluorenylmethoxycarbonyl)-L-prolylglycolate 
• 139578-71-5 (S)-Pyrrolidine-1,2-dicarboxylic acid 2-[(2S,6R)-6-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-4-trityl-morpholin-2-ylmethyl] ester 1-(9H-fluoren-9-ylmethyl) ester 
• 126771-49-1 (S)-Pyrrolidine-1,2-dicarboxylic acid 2-[4-(2,4-dichloro-phenoxycarbonylmethoxy)-benzyl] ester 1-(9H-fluoren-9-ylmethyl) ester 
• 147221-36-1 Fmoc-ProOPp 
• 120061-00-9 Fmoc-Pro-MePhe-Thz-OTmse 
• 103321-52-4 (S)-N-(fluoren-9-ylmethoxycarbonyl)prolyl chloride 
• 114119-85-6 Fmoc-Pro-ODhbt 

Relevant articles and documents

Versatile Methods to Dispense Submilligram Quantities of Solids Using Chemical-Coated Beads for High-Throughput Experimentation

High-throughput experimentation is a technique for screening multiple reaction conditions in parallel at micro or nanoscale without depleting precious starting materials. However, assembling a comprehensive screening set often involves the distribution of large number of solid reagents with diverse physical properties in small quantities. Automated solid dispensing, especially at submilligram scale, has long been a challenge with no practical and reliable solutions. This paper describes the use of our newly developed chemical-coated beads technology to provide a universal approach to the solid handling problem. This technology, when combined with an automated solid dispensing platform or calibrated scoops, can dispense submilligram quantities of a variety of solids with efficiency and adequate accuracy.

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.

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.