CAS 144120-54-7

1-(2-Propen-1-yl) hydrogen N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-glutamate

Description:

1-(2-Propen-1-yl) hydrogen N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-glutamate, with CAS number 144120-54-7, is a synthetic compound primarily used in peptide chemistry and bioconjugation applications. This substance features a propenyl group, which contributes to its reactivity, particularly in Michael addition reactions. The presence of the fluorenylmethoxycarbonyl (Fmoc) protecting group indicates its utility in solid-phase peptide synthesis, where it serves to protect the amino group of L-glutamate during the synthesis process. The compound is characterized by its ability to undergo various chemical transformations, making it valuable in the development of peptide-based therapeutics. Additionally, it exhibits solubility in organic solvents, which is typical for compounds containing aromatic groups. Its structural complexity allows for specific interactions in biological systems, potentially influencing its pharmacological properties. Overall, this compound is significant in the field of medicinal chemistry and peptide synthesis, facilitating the creation of complex biomolecules for research and therapeutic purposes.

Formula: C₂₃H₂₃NO₆

InChI: InChI=1/C23H23NO6/c1-2-13-29-22(27)20(11-12-21(25)26)24-23(28)30-14-19-17-9-5-3-7-15(17)16-8-4-6-10-18(16)19/h2-10,19-20H,1,11-14H2,(H,24,28)(H,25,26)/t20-/m0/s1

InChI key: InChIKey=ORKKMGRINLTBPC-FQEVSTJZSA-N

SMILES: C(OC(N[C@H](C(OCC=C)=O)CCC(O)=O)=O)C1C=2C(C=3C1=CC=CC3)=CC=CC2

Synonyms:

• (4S)-4-(9H-Fluoren-9-ylmethoxycarbonylamino)-5-oxo-5-prop-2-enoxypentanoic acid
• (4S)-4-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-5-oxo-5-(prop-2-en-1-yloxy)pentanoic acid (non-preferred name)
• 1-(2-Propen-1-yl) hydrogen N-[(9H-fluoren-9-ylmethoxy)carbonyl]-<span class="text-smallcaps">L</span>-glutamate
• <span class="text-smallcaps">L</span>-Glutamic acid, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-, 1-(2-propen-1-yl) ester
• <span class="text-smallcaps">L</span>-Glutamic acid, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-, 1-(2-propenyl) ester
• Fmoc-Glu-OAll
• Fmoc-Glu-allyl ester
• Fmoc-L-glutamic acid α-allyl ester
• 1-(2-Propen-1-yl) hydrogen N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-glutamate
• L-Glutamic acid, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-, 1-(2-propen-1-yl) ester
• L-Glutamic acid, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-, 1-(2-propenyl) ester
• FMOC-GLUTAMIC ACID-ALLYL ESTER
• N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-L-GLUTAMIC-ACID-ALPHA ALLYL ESTER
• FMOC-GLU-OAL
• FMOC-GLU(OME)-OH
• FMOC-L-GLUTAMIC ACID ALPHA-ALLYL ESTER
• N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-L-GLUTAMIC ACID ALPHA-ALLYL ESTER
• N-ALPHA-FMOC-L-GLUTAMIC ACID ALPHA-ALLYL ESTER
• FMOC-L-GLUTAMIC ACID 1-ALLYL ESTER

1-Allyl N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-glutamate

CAS: 144120-54-7

Formula: C₂₃H₂₃NO₆

Purity: >96.0%(T)(HPLC)

Color and Shape: White to Almost white powder to crystal

Molecular weight: 409.44

Ref: 3B-A2909

N-Fmoc-L-glutamic acid 1-allyl ester, 98%

CAS: 144120-54-7

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Sci

Formula: C₂₃H₂₃NO₆

Purity: 98%

Molecular weight: 409.44

Ref: 02-H66448

Fmoc-Glu-allyl ester

CAS: 144120-54-7

α-Allyl esters are of special interest, because they are a useful tool for the on-resin synthesis of head-to-tail cyclic peptides, side-chain lactam peptides, glyco- and sulfo-peptides, and branched peptides. Allyl esters are cleaved quantitatively under mild conditions using Pd(0). These conditions are compatible with Fmoc- and Boc-SPPS. Fmoc-Glu-OAll is a versatile educt for the synthesis of N-modified glutamines. Due to the lack of steric hindrance of the allyl group, prolonged treatment with harsher Fmoc cleavage agents or even piperidine may induce side-reactions as glutarimide formation, as observed by Zhu and Marchant.

Formula: C₂₃H₂₃NO₆

Purity: 99.03%

Color and Shape: White Powder

Molecular weight: 409.44

Ref: 01-4026433

L-Glutamic acid, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-, 1-(2-propen-1-yl) ester

CAS: 144120-54-7

Formula: C₂₃H₂₃NO₆

Purity: 95%

Color and Shape: Solid

Molecular weight: 409.4318

Ref: IN-DA001IZI

Fmoc-L-Glutamic Acid 1-Allyl Ester

CAS: 144120-54-7

Fmoc-L-Glutamic Acid 1-Allyl Ester

Purity: 98%

Molecular weight: 409.43g/mol

Ref: 54-OR1013369

Fmoc-Glu-OAll

CAS: 144120-54-7

Formula: C₂₃H₂₃NO₆

Molecular weight: 409.43

Ref: 7W-GM2584

Fmoc-L-glutamic acid 1-allyl ester

CAS: 144120-54-7

Purity: 95%

Color and Shape: Solid

Molecular weight: 409.44

Ref: 10-M06240

Fmoc-glu-OAll

CAS: 144120-54-7

Fmoc-glu-OAll is a cyclic peptide that is synthesized using solid-phase synthesis. It has been shown to have minimal inhibitory concentration (MIC) values of 0.5 µg/mL against mouse tumor cells and human serum, as well as high affinity for integrin receptors. This peptide also binds to the human serum albumin and blood clotting factor Xa, which are proteins involved in cancer therapy.

Formula: C₂₃H₂₃NO₆

Purity: Min. 95%

Molecular weight: 409.43 g/mol

Ref: 3D-FF41629