Fmoc-Glu(OtBu)-OH - ≥98% , CAS No.71989-18-9

CAS: 71989-18-9 Cat. No.: F100413 Molecular Weight: 425.47 Beilstein Registry Number: 3636375 EC Number: 276-253-8

GRADE & PURITY ≥98%

Synonyms

5-tert-Butyl N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-glutamate | AS-14175 | Fmoc-Glu(OtBu)-OH, >=98.0% (HPLC) | HY-Y0134 | STL466194 | (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-[(2-methylpropan-2-yl)oxy]-5-oxopentanoic acid | 5-tert-Butyl N-Fmoc-L-glu

Storage

Store at 2-8°C,Protected from light

Shipped In

Wet ice

Overview

• Ligand in the synthesis of cis-substituted cyclopropane carboxylic acids via C-H activation of cyclopropane carboxamides using Pd catalyst. 

• Linker in the preparation of multi-small molecule-conjugated PTX (paclitaxel) derivatives. 

It can be also used as a building block in the preparation of stapled α-helical peptides  and peptide C-terminal thioesters 

Specifications

Synonyms

5-tert-Butyl N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-glutamate | AS-14175 | Fmoc-Glu(OtBu)-OH, >=98.0% (HPLC) | HY-Y0134 | STL466194 | (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-[(2-methylpropan-2-yl)oxy]-5-oxopentanoic acid | 5-tert-Butyl N-Fmoc-L-glu

Specifications & Purity

≥98%

Storage

Store at 2-8°C, Protected from light

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 504760911
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504760911
• Canonical Smiles: CC(C)(C)OC(=O)CCC(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• IUPAC Name: (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-[(2-methylpropan-2-yl)oxy]-5-oxopentanoic acid
• InChIKey: OTKXCALUHMPIGM-FQEVSTJZSA-N
• INCHI: 1S/C24H27NO6/c1-24(2,3)31-21(26)13-12-20(22(27)28)25-23(29)30-14-19-17-10-6-4-8-15(17)16-9-5-7-11-18(16)19/h4-11,19-20H,12-14H2,1-3H3,(H,25,29)(H,27,28)/t20-/m0/s1
• Isomeric SMILES: CC(C)(C)OC(=O)CC[C@@H](C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• WGK Germany: 3
• Molecular Weight: 425.47
• Beilstein: 3636375
• Reaxy-Rn: 9874580
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=9874580&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Amino acids and derivatives
          • Level6 Alpha amino acids and derivatives
            • Level7 Glutamic acid and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Amino acids and derivatives - Alpha amino acids and derivatives
• Direct Parent: Glutamic acid and derivatives
• Alternative Parents: Fluorenes Fatty acid esters Dicarboxylic acids and derivatives Carbamate esters Organic carbonic acids and derivatives Carboxylic acid esters Carboxylic acids Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic homopolycyclic compounds
• Substituents: Glutamic acid or derivatives - Fluorene - Fatty acid ester - Dicarboxylic acid or derivatives - Fatty acyl - Benzenoid - Carbamic acid ester - Carboxylic acid ester - Carbonic acid derivative - Carboxylic acid - Carbonyl group - Organonitrogen compound - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Aromatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as glutamic acid and derivatives. These are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: Soluble in Methanol
• Sensitivity: light sensitive
• Specific Rotation[α]: -8 ° (C=1, MeOH)
• Melt Point(°C): 83-90°C
• Molecular Weight: 425.500 g/mol
• XLogP3: 3.900
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 425.184 Da
• Monoisotopic Mass: 425.184 Da
• Topological Polar Surface Area: 102.000 Ų
• Heavy Atom Count: 31
• Formal Charge: 0
• Complexity: 635.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Like Lin, Cong Li, Yujiao Zhang, Li Zhang, Lu Gao, Lihua Jin, Yu Shu, Yehua Shen.  (2024)  Effect of Akt-activating peptide obtained from walnut protein degradation on the prevention of memory impairment in mice.  Food & Function,      [PMID:38305469] [10.1039/D3FO04479C]