(S)-N-Fmoc-2-(2'-propylenyl)alanine

Base Information

• Chemical Name: (S)-N-Fmoc-2-(2'-propylenyl)alanine
• CAS No.: 288617-71-0
• Molecular Formula: C21H21NO4
• Molecular Weight: 351.3957
• Mol file: 288617-71-0.mol

Synonyms:(S)-N-Fmoc-2-(2'-propylenyl)alanine;

Chemical Property of (S)-N-Fmoc-2-(2'-propylenyl)alanine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.595
• Boiling Point: 564.259 °C at 760 mmHg
• PKA: 3.81±0.11(Predicted)
• Flash Point: 295.054 °C
• PSA: 75.63000
• Density: 1.224 g/cm³
• LogP: 4.33540
• Storage Temp.: ?20°C

Purity/Quality:

98%,99%, ^*data from raw suppliers

Fmoc-alpha-methyl-L-allylglycine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N
• Hazard Codes: N
• Statements: 50
• Safety Statements: 61

MSDS Files:

SDS file from LookChem

Useful:

• 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.

Technology Process of (S)-N-Fmoc-2-(2'-propylenyl)alanine

There total 7 articles about (S)-N-Fmoc-2-(2'-propylenyl)alanine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + Cα-methyl-D-allylglycine (96886-56-5) → (R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpent-4-enoic acid (288617-71-0,288617-76-5)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; water; at 20 ℃;

DOI:10.1021/acs.jmedchem.6b01796

Reference yield:

2-(tert-butoxycarbonylmethyl-amino)-2-methyl-pent-4-enoic acid + 9-fluorenylmethyl carbamate (84418-43-9) → (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpent-4-enoic acid (288617-71-0,288617-76-5)

Guidance literature:

2-(tert-butoxycarbonylmethyl-amino)-2-methyl-pent-4-enoic acid; In dichloromethane; trifluoroacetic acid; at 0 ℃; for 0.5h;

9-fluorenylmethyl carbamate; With sodium carbonate; In water; acetone; at 20 ℃; for 12h; Further stages.;

DOI:10.1021/ja000563a

Reference yield:

2-(tert-butoxycarbonylmethyl-amino)-2-methyl-pent-4-enoic acid + 9-fluorenylmethyl carbamate (84418-43-9) → (R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpent-4-enoic acid (288617-71-0,288617-76-5)

Guidance literature:

2-(tert-butoxycarbonylmethyl-amino)-2-methyl-pent-4-enoic acid; In dichloromethane; trifluoroacetic acid; at 0 ℃; for 0.5h;

9-fluorenylmethyl carbamate; With sodium carbonate; In water; acetone; at 20 ℃; for 12h; Further stages.;

DOI:10.1021/ja000563a

upstream raw materials:

9-fluorenylmethyl carbamate

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

(S)-α-allylalanine

C^α-methyl-D-allylglycine

Downstream raw materials:

C₇₄H₁₁₀N₁₈O₁₄

Refernces

• 1、 Karatas, Hacer,Li, Yangbing,Liu, Liu,Ji, Jiao,Lee, Shirley,Chen, Yong,Yang, Jiuling,Huang, Liyue,Bernard, Denzil,Xu, Jing,Townsend, Elizabeth C.,Cao, Fang,Ran, Xu,Li, Xiaoqin,Wen, Bo,Sun, Duxin,Stuckey, Jeanne A,Lei, Ming,Dou, Yali,Wang, Shaomeng. "Discovery of a Highly Potent, Cell-Permeable Macrocyclic Peptidomimetic (MM-589) Targeting the WD Repeat Domain 5 Protein (WDR5)-Mixed Lineage Leukemia (MLL) Protein-Protein Interaction". . p. 4818 - 4839. Retrieved 2017/06/28.
• 2、 Long, Ya-Qiu,Huang, Shao-Xu,Zawahir, Zahrah,Xu, Zhong-Liang,Li, Huiyuan,Sanchez, Tino W.,Zhi, Ying,De Houwer, Stephanie,Christ, Frauke,Debyser, Zeger,Neamati, Nouri. "Design of cell-permeable stapled peptides as HIV-1 integrase inhibitors". . p. 5601 - 5612. Retrieved 2013/07/26.