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(S)-N-Fmoc-2-(2'-propylenyl)alanine is a specialized amino acid derivative used in the field of peptide chemistry. It is characterized by the presence of an olefinic side chain, which allows for the creation of stable peptide structures through a process known as peptide stapling. This unique property makes it a valuable compound for the development of novel therapeutic peptides with enhanced stability and cellular uptake.

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  • (S)-2-((((9H-FLUOREN-9-YL)METHOXY)CARBONYL)AMINO)-2-METHYLPENT-4-ENOIC ACID

    Cas No: 288617-71-0

  • USD $ 1.9-2.9 / Gram

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  • 1000 Metric Ton/Month

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  • 288617-71-0 Structure
  • Basic information

    1. Product Name: (S)-N-Fmoc-2-(2'-propylenyl)alanine
    2. 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
    3. CAS NO:288617-71-0
    4. Molecular Formula: C21H21NO4
    5. Molecular Weight: 351.4
    6. EINECS: N/A
    7. Product Categories: α-Methyl Amino Acids
    8. Mol File: 288617-71-0.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 564.259 °C at 760 mmHg
    3. Flash Point: 295.054 °C
    4. Appearance: /
    5. Density: 1.224
    6. Vapor Pressure: 0mmHg at 25°C
    7. Refractive Index: 1.595
    8. Storage Temp.: ?20°C
    9. Solubility: N/A
    10. PKA: 3.81±0.11(Predicted)
    11. CAS DataBase Reference: (S)-N-Fmoc-2-(2'-propylenyl)alanine(CAS DataBase Reference)
    12. NIST Chemistry Reference: (S)-N-Fmoc-2-(2'-propylenyl)alanine(288617-71-0)
    13. EPA Substance Registry System: (S)-N-Fmoc-2-(2'-propylenyl)alanine(288617-71-0)
  • Safety Data

    1. Hazard Codes: N
    2. Statements: 50
    3. Safety Statements: 61
    4. RIDADR: UN 3077 9 / PGIII
    5. WGK Germany: 3
    6. RTECS:
    7. TSCA: No
    8. HazardClass: N/A
    9. PackingGroup: N/A
    10. Hazardous Substances Data: 288617-71-0(Hazardous Substances Data)

288617-71-0 Usage

Uses

Used in Pharmaceutical Industry:
(S)-N-Fmoc-2-(2'-propylenyl)alanine is used as a building block for the synthesis of stapled peptides. The incorporation of this amino acid into a peptide sequence, along with another of the same or a derivative with a different length of the olefinic side chain, enables the formation of a stable alpha-helical structure through a ring-closing metathesis reaction using Grubbs' catalyst. This process results in a stapled peptide macrocycle, which has been shown to exhibit increased proteolytic stability and enhanced cellular uptake, making it a promising approach for the development of new drugs with improved efficacy and safety profiles.
Used in Research and Development:
In the field of research and development, (S)-N-Fmoc-2-(2'-propylenyl)alanine serves as an essential tool for studying the structure-function relationships of peptides and proteins. By incorporating this amino acid into peptide sequences, researchers can investigate the effects of peptide stapling on protein-protein interactions, protein stability, and cellular signaling pathways. This information can be crucial for understanding the underlying mechanisms of various diseases and for the design of targeted therapeutic strategies.
Used in Drug Design and Optimization:
(S)-N-Fmoc-2-(2'-propylenyl)alanine is used as a key component in the design and optimization of peptide-based drugs. The ability to create stable alpha-helical structures through peptide stapling allows for the development of peptides with enhanced biological activity and selectivity. This can lead to the discovery of novel therapeutic agents with improved pharmacokinetic properties, reduced off-target effects, and increased resistance to degradation by proteolytic enzymes.

Check Digit Verification of cas no

The CAS Registry Mumber 288617-71-0 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,8,8,6,1 and 7 respectively; the second part has 2 digits, 7 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 288617-71:
(8*2)+(7*8)+(6*8)+(5*6)+(4*1)+(3*7)+(2*7)+(1*1)=190
190 % 10 = 0
So 288617-71-0 is a valid CAS Registry Number.
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

288617-71-0 Well-known Company Product Price

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  • Aldrich

  • (F6062)  Fmoc-(S)-2-(2-propenyl)Ala-OH  

  • 288617-71-0

  • F6062-1G

  • 3,879.72CNY

  • Detail
  • Aldrich

  • (F6062)  Fmoc-(S)-2-(2-propenyl)Ala-OH  

  • 288617-71-0

  • F6062-5G

  • 15,257.97CNY

  • Detail

288617-71-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-2-methylpent-4-enoic acid

1.2 Other means of identification

Product number -
Other names Fmoc-(S)-2-(2-propenyl)Ala-OH

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:288617-71-0 SDS

288617-71-0Relevant articles and documents

PEPTIDOMIMETIC INHIBITORS OF THE WDR5-MLL INTERACTION

-

Paragraph 0240; 0244; 0245, (2018/12/13)

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.

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

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

, p. 4818 - 4839 (2017/06/28)

We report herein the design, synthesis, and evaluation of macrocyclic peptidomimetics that bind to WD repeat domain 5 (WDR5) and block the WDR5-mixed lineage leukemia (MLL) protein-protein interaction. Compound 18 (MM-589) binds to WDR5 with an IC50 value of 0.90 nM (Ki value 50 value of 12.7 nM. Compound 18 potently and selectively inhibits cell growth in human leukemia cell lines harboring MLL translocations and is >40 times better than the previously reported compound MM-401. Cocrystal structures of 16 and 18 complexed with WDR5 provide structural basis for their high affinity binding to WDR5. Additionally, we have developed and optimized a new AlphaLISA-based MLL HMT functional assay to facilitate the functional evaluation of these designed compounds. Compound 18 represents the most potent inhibitor of the WDR5-MLL interaction reported to date, and further optimization of 18 may yield a new therapy for acute leukemia.

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

Zhang, Qingzhou,Shi, Xiaodong,Jiang, Yanhong,Li, Zigang

, p. 7621 - 7626 (2014/12/11)

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.

Design of cell-permeable stapled peptides as HIV-1 integrase inhibitors

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

, p. 5601 - 5612 (2013/07/26)

HIV-1 integrase (IN) catalyzes the integration of viral DNA into the host genome, involving several interactions with the viral and cellular proteins. We have previously identified peptide IN inhibitors derived from the α-helical regions along the dimeric interface of HIV-1 IN. Herein, we show that appropriate hydrocarbon stapling of these peptides to stabilize their helical structure remarkably improves the cell permeability, thus allowing inhibition of the HIV-1 replication in cell culture. Furthermore, the stabilized peptides inhibit the interaction of IN with the cellular cofactor LEDGF/p75. Cellular uptake of the stapled peptide was confirmed in four different cell lines using a fluorescein-labeled analogue. Given their enhanced potency and cell permeability, these stapled peptides can serve as not only lead IN inhibitors but also prototypical biochemical probes or nanoneedles for the elucidation of HIV-1 IN dimerization and host cofactor interactions within their native cellular environment.

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