23009-50-9

Basic information

• Product Name: trans-4-Methyl-L-proline
• Synonyms: trans-4-Methyl-L-proline;(2S,4R)-4-methylpyrrolidine-2-carboxylic acid
• CAS NO: 23009-50-9
• Molecular Formula: C₆H₁₁NO₂
• Molecular Weight: 129.15704
• Mol File: 23009-50-9.mol
• Article Data: 10

Chemical Properties

• Melting Point: 230-238 °C
• Boiling Point: 250.2±33.0 °C(Predicted)
• Appearance: /
• Density: 1.104±0.06 g/cm3(Predicted)
• PKA: 2.36±0.40(Predicted)
• CAS DataBase Reference: trans-4-Methyl-L-proline(CAS DataBase Reference)
• NIST Chemistry Reference: trans-4-Methyl-L-proline(23009-50-9)
• EPA Substance Registry System: trans-4-Methyl-L-proline(23009-50-9)

Safety Data

• Hazardous Substances Data: 23009-50-9(Hazardous Substances Data)

Upstream product

• 220047-73-4 (2S,4R)-1-tert-butoxycarbonyl-2-benzyloxymethyl-4-methylpyrrolidine 
• 61-90-5 L-leucine 
• 165273-05-2 trans-4-methyl-L-proline ethyl ester 
• 1027101-89-8 N-CBz-trans-4-methyl-L-proline ethyl ester 
• 169820-06-8 N-CBz-4-exo-methylene-L-proline ethyl ester 
• 83507-89-5 N-<(phenylmethoxy)carbonyl>-4-oxo-(S)-proline ethyl ester 
• 103667-57-8 (2S,4R)-ethyl N¹-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylate 
• 61478-25-9 (2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid ethyl ester 
• 51-35-4 4R-4-hydroxyproline 
• 2743-60-4 L-Leucine ethyl ester 
• 119595-73-2 L-α-tert-butyl γ-methyl N-(9-(9-phenylfluorenyl))glutamate 
• 119595-72-1 L-N-(9-(9-phenylfluorenyl))glutamic acid γ-methylester 
• 1499-55-4 L-glutamic acid 5-methyl ester 
• 212266-68-7 ((R)-2-Benzenesulfonyl-1-benzyloxymethyl-ethyl)-benzyl-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-amine 

Downstream Products

• 333777-34-7 (2S,4R)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-4-methylpyrrolidine-2-carboxylic acid 
• 901139-63-7 N-9-fuorenylmethoxycarbonyl-(2S,4R)-4-methylprolyl-(2S,4S)-4-methylprolyl-glycine benzyl ester 
• 901138-97-4 N-9-fuorenylmethoxycarbonyl-(2S,4R)-4-methylprolyl-(2S)-prolyl-glycine benzyl ester 

Relevant articles and documents

Evolution of Biocatalytic and Chemocatalytic C-H Functionalization Strategy in the Synthesis of Manzacidin C

Because of their unique molecular architecture, the manzacidins have been the subject of intense synthetic efforts in the past two decades. Here, we describe two synthetic approaches toward manzacidin C that center on the enzymatic hydroxylation of unprotected l-leucine. This study also resulted in the discovery of novel synthetic methodologies, including a photocatalytic C-H azidation of unprotected amino acids. Additionally, we describe the use of hydroxylated l-leucine in the preparation of various densely substituted pyrrolidines.

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.

Reciprocity of steric and stereoelectronic effects in the collagen triple helix

In previous work, we demonstrated that 4-fluoroproline residues can contribute greatly to the conformational stability of the collagen triple helix, and that this stability arises from stereoelectronic effects that fix the pucker of the pyrrolidine ring and thereby preorganize the backbone properly for triple-helix formation. Here, we take a reciprocal approach, demonstrating that the steric effect of a 4-methyl group confers stability similar to that from a 4-fluoro group in the opposite configuration. Such fundamental interplay between steric and stereoelectronic effects is heretofore unknown in proteinsnatural or syntheticand provides a new means to modulate conformational stability. Copyright