(R)-N-Fmoc-2-(4'-pentenyl)glycine

Name: (R)-N-Fmoc-2-(4'-pentenyl)glycine
Brand: ChemScene
Availability: InStock
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CAS No. 1093645-21-6
Cat. No. CS-0100562
Molecule weight365.42
Purity≥95%
MDL No.MFCD17215632

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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(R)-N-Fmoc-2-(4'-pentenyl)glycine|CS-0100562

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General Information

CAS No. 1093645-21-6
Cat. No. CS-0100562
Purity ≥95%
MDL No. MFCD17215632
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₂H₂₃NO₄
Molecular Weight 365.42
Synonym(s) Fmoc-R5H-OH
SMILES C=CCCC[C@@H](NC(OCC1C2=C(C3=C1C=CC=C3)C=CC=C2)=O)C(O)=O

Description

(R)-N-Fmoc-2-(4'-pentenyl)glycine features a chiral glycine scaffold with a pendant 4'-pentenyl side chain, enabling site-specific conjugation via click chemistry. The Fmoc group ensures efficient solid-phase peptide synthesis, while the terminal alkene supports bioorthogonal coupling. This building block integrates seamlessly into peptidomimetics and functionalized biomolecules under standard conditions.

Application

(R)-N-Fmoc-2-(4'-pentenyl)glycine serves as a versatile building block for peptide synthesis, enabling the incorporation of a terminal alkenyl side chain at the Cα position. The Fmoc group provides reliable orthogonal protection for primary amines during solid-phase peptide synthesis, while the pendant pentenyl moiety facilitates subsequent functionalization via click chemistry or transition-metal-catalyzed coupling. Its bench-stable nature and compatibility with standard purification protocols make it well-suited for iterative synthesis workflows in medicinal chemistry and macrocycle construction.

Synthesis

Route1
- 1093645-18-1
- ~%
- In-stock
  
  1093645-21-6
References
- Ingenito, Raffaele; Burton, Charlotte; Langella, Annunziata; Chen, Xun; Zytko, Karolina; Pessi, Antonello; Wang, Jun; Bianchi, Elisabetta Bioorganic and Medicinal Chemistry Letters, 2010 , vol. 20, # 1 p. 236 - 239

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

TPSA 75.63
LogP 4.3346
H_Acceptors 3
H_Donors 2
Rotatable_Bonds 8

Other Classifications

Building Blocks Functional Group Fmoc

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Life Science Amino Acids and their Derivatives Alanine and derivatives

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

Key Words

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(R)-N-Fmoc-2-(4'-pentenyl)glycine

CAS No. 1093645-21-6

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