333777-34-7

Basic information

• Product Name: (2S,4R)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-4-methylpyrrolidine-2-carboxylic acid
• Synonyms: (2S,4R)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-4-methylpyrrolidine-2-carboxylic acid
• CAS NO: 333777-34-7
• Molecular Weight: 351.402
• Mol File: 333777-34-7.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (2S,4R)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-4-methylpyrrolidine-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,4R)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-4-methylpyrrolidine-2-carboxylic acid(333777-34-7)
• EPA Substance Registry System: (2S,4R)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-4-methylpyrrolidine-2-carboxylic acid(333777-34-7)

Safety Data

• Hazardous Substances Data: 333777-34-7(Hazardous Substances Data)

Usage

Description

(2S,4R)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-4-methylpyrrolidine-2-carboxylic acid, also known as Fmoc-D-MePro-OH, is a compound utilized in organic chemistry, particularly in the synthesis of peptides and proteins. It serves as a protecting group for amino acids, with its Fmoc group allowing for easy removal under mild acidic conditions. The presence of a pyrrolidine ring and a fluorenyl group in its chemical structure enhances its stability and reactivity in chemical reactions. (2S,4R)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-4-methylpyrrolidine-2-carboxylic acid is a vital building block for the preparation of complex peptides and significantly contributes to biochemical research and drug development.

Uses

Used in Pharmaceutical Industry:
Fmoc-D-MePro-OH is used as a protecting group in the synthesis of peptides and proteins for drug development. Its ability to be easily removed under mild acidic conditions facilitates the controlled assembly of complex peptide structures, which is crucial for the creation of potential therapeutic agents.
Used in Biochemical Research:
In biochemical research, Fmoc-D-MePro-OH is employed as a component in the synthesis of custom peptides and proteins. Its stability and reactivity support the exploration of novel biochemical pathways and the development of new diagnostic tools and therapeutic strategies.
Used in Organic Chemistry:
Fmoc-D-MePro-OH is utilized in various organic chemistry applications, such as the synthesis of complex organic molecules and the development of new chemical reactions. Its unique structure and properties make it a valuable compound for advancing the field of organic chemistry.

Upstream product

• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 23009-50-9 trans-4-methyl-L-proline 
• 365280-18-8 trans-4-methyl-L-proline hydrochloride 
• 61-90-5 L-leucine 
• 98-79-3 L-Pyroglutamic acid 
• 108963-96-8 (S)-1-tert-butoxycarbonyl-5-methoxycarbonyl-pyrrolidin-2-one 
• 196394-49-7 (2S,4R)-1-(tert-butyl) 2-methyl 4-methyl-5-oxopyrrolidine-1,2-dicarboxylate 
• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 871727-77-4 N-Boc-4-methyl-L-proline 
• 1228577-05-6 (2S,4R)-4-methyl N-[(9-fluorenyl)-methoxycarbonyl]-proline tert-butyl ester 
• 364750-80-1 (2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid 

Downstream Products

• 901138-97-4 N-9-fuorenylmethoxycarbonyl-(2S,4R)-4-methylprolyl-(2S)-prolyl-glycine benzyl ester 
• 901139-63-7 N-9-fuorenylmethoxycarbonyl-(2S,4R)-4-methylprolyl-(2S,4S)-4-methylprolyl-glycine benzyl ester 

Relevant articles and documents

A lanthanide(III) triflate mediated macrolactonization/solid-phase synthesis approach for depsipeptide synthesis

The effect of dysprosium(III) triflate on macrolactonization reactions to form depsipeptides using MNBA (Shiina's reagent) is reported. Improved yields were obtained for the formation of 16-membered depsipeptides using lanthanide triflate additives. The use of a macrocyclization strategy permits the use of a semiautomated solid-phase synthesis approach for the rapid synthesis of analogues of the antibacterial A54556 acyldepsipeptides in only two physical operations, requiring only final product purification after cyclization.

A one-pot chemoenzymatic synthesis of (2S, 4R)-4-methylproline enables the first total synthesis of antiviral lipopeptide cavinafungin B

We report an efficient ten-step (longest linear sequence) synthesis of antiviral natural product cavinafungin B in 37% overall yield. By leveraging a one-pot chemoenzymatic synthesis of (2S,4R)-4-methylproline and oxazolidine-tethered (AT (Boc)G-Rink resin) SPPS methodology, the assembly of our molecular target could be conducted in an efficient manner. This general strategy could prove amenable to the construction of other natural and unnatural linear lipopeptides. The value of incorporating biocatalytic steps in complex molecule synthesis is highlighted by this work.

Collagen mimics

Novel collagen mimics are disclosed with a tripeptide unit having the formula (Xaa-Yaa-Gly)n, where one of the positions Xaa or Yaa is a bulky, non-electron withdrawing proline derivative. By substituting a proline derivative at either the Xaa or Yaa position in the native collagen helix, the stability of the helix is increased due solely to steric effects relative to prior known collagen-related triple helices. Methods are also disclosed for making the novel collagen mimics.