288617-71-0

Basic information

• Product Name: (S)-N-Fmoc-2-(2'-propylenyl)alanine
• Synonyms: (S)-N-Fmoc-2-(2'-propylenyl)alanine;(S)-N-(9-Fluorenylmethylcarbamate)-2-(2'-propylenyl)alanine;Fmoc-alpha-methyl-L-allylglycine;(2S)-2-[[(9H-Fluoren-9-ylmethoxy)carbonyl]amino]-2-methyl-4-pentenoic acid;(S)-N-Fmoc-alpha-allylalanine;FMoc-α-Me-Gly(Allyl)-OH;(S)-N-Fmoc-α-2-n-propenylalanine;Fmoc-(S)-2-(2-propenyl)alanine
• CAS NO: 288617-71-0
• Molecular Formula: C21H21NO4
• Molecular Weight: 351.4
• Product Categories: α-Methyl Amino Acids
• Mol File: 288617-71-0.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 564.259 °C at 760 mmHg
• Flash Point: 295.054 °C
• Appearance: /
• Density: 1.224
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.595
• Storage Temp.: ?20°C
• PKA: 3.81±0.11(Predicted)
• CAS DataBase Reference: (S)-N-Fmoc-2-(2'-propylenyl)alanine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-N-Fmoc-2-(2'-propylenyl)alanine(288617-71-0)
• EPA Substance Registry System: (S)-N-Fmoc-2-(2'-propylenyl)alanine(288617-71-0)

Safety Data

• Hazard Codes: N
• Statements: 50
• Safety Statements: 61
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• TSCA: No
• Hazardous Substances Data: 288617-71-0(Hazardous Substances Data)

Usage

Uses

Olefinic alpha-methyl amino acid for peptide stapling. Upon incorporation of this amino acid into a peptide, along with another of the same or derivative with a different length of the olefinic side chain, the two can be ′stapled′ via a ring closing metathesis reaction with Grubb′s catalyst (product # 579726). The resulting stapled peptide macrocycle has been shown to stabilize the alpha-helical structure of peptides, which can lead to favorable biological characteristics such as increased proteolytic stability and cellular uptake.

InChI:InChI=1/C21H21NO4/c1-3-12-21(2,19(23)24)22-20(25)26-13-18-16-10-6-4-8-14(16)15-9-5-7-11-17(15)18/h3-11,18H,1,12-13H2,2H3,(H,22,25)(H,23,24)/t21-/m0/s1

Upstream product

• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 96886-56-5 C^α-methyl-D-allylglycine 
• 84418-43-9 9-fluorenylmethyl carbamate 
• 96886-55-4 (S)-α-allylalanine 

Downstream Products

• 1445137-67-6 C₇₄H₁₁₀N₁₈O₁₄ 
• 71785-67-6 (R)-2-Amino-2-(2-propenyl)propionsaeure-methylester 

Relevant articles and documents

PEPTIDOMIMETIC INHIBITORS OF THE WDR5-MLL INTERACTION

The present disclosure provides compounds represented by Formula I: and the pharmaceutically acceptable salts and solvates thereof, wherein R1, R2, R3a, R3b, R4a, R4b, R5a, and R5b are as defined as set forth in the specification. The present disclosure also provides compounds of Formula I for use to treat a condition, disease, or disorder responsive to inhibition of the WDR5 interaction with its binding partners including, but not limited to, the WDR5-MLL protein-protein interaction.

Influence of α-methylation in constructing stapled peptides with olefin metathesis

Ring-closing metathesis is commonly utilized in peptide macro-cyclization. The influence of α-methylation of the amino acids bearing the olefin moieties has never been systematically studied. In this report, controlled reactions unambiguously indicate that α-methylation at the N-terminus of the metathesis sites is crucial for this reaction to occur. Also, we first elucidated that the E-isomers of stapled peptides are significantly more helical than the Z-isomers.

An all-hydrocarbon cross-linking system for enhancing the helicity and metabolic stability of peptides [8]

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