(4R)-1-Fmoc-4-(allyloxycarbonylamino)-L-proline

Name: (4R)-1-Fmoc-4-(allyloxycarbonylamino)-L-proline
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CAS No. 273222-05-2
Cat. No. CS-0312165
Molecule weight436.46
Purity≥95%
MDL No.MFCD01860708

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(4R)-1-Fmoc-4-(allyloxycarbonylamino)-L-proline|CS-0312165

Structure of 273222-05-2

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General Information

CAS No. 273222-05-2
Cat. No. CS-0312165
Purity ≥95%
MDL No. MFCD01860708
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₄H₂₄N₂O₆
Molecular Weight 436.46
Synonym(s) (2S,4R)-1-(9H-fluoren-9-ylmethoxycarbonyl)-4-(prop-2-enoxycarbonylamino)pyrrolidine-2-carboxylic acid
SMILES O=C(N1[C@@H](C[C@H](C1)NC(OCC=C)=O)C(O)=O)OCC2C3=CC=CC=C3C4=CC=CC=C42

Description

(4R)-1-Fmoc-4-(allyloxycarbonylamino)-L-proline is a stereochemically defined proline derivative featuring a fluorous (Fmoc) protecting group at the N-terminus and an allyloxycarbonyl moiety on the pyrrolidine ring. This configuration enables selective conjugation via click chemistry while maintaining stability under standard peptide synthesis conditions. The molecule integrates readily into peptidomimetic scaffolds and facilitates site-specific derivatization in synthetic biology applications.

Application

(4R)-1-Fmoc-4-(allyloxycarbonylamino)-L-proline serves as a versatile proline-based building block for peptide synthesis, enabling site-specific incorporation of allyl-containing side chains. The Fmoc group provides orthogonal protection for the amine, while the allyloxycarbonyl moiety offers a handle for subsequent functionalization via palladium-catalyzed reactions. This derivative exhibits excellent bench stability and facilitates efficient purification by standard chromatographic methods, making it well-suited for solid-phase and solution-phase peptide assembly workflows.

Safety Information

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GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302
Precautionary Statements : P264-P270-P330-P501

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Computational Chemistry Data

TPSA 105.17
LogP 3.3752
H_Acceptors 5
H_Donors 2
Rotatable_Bonds 6

Other Classifications

Building Blocks Functional Group Amine

Building Blocks Functional Group Carboxylic Acid

Building Blocks Functional Group Olefins

Building Blocks Functional Group Ester

Building Blocks Skeleton Aliphatic heterocycle compounds Pyrrolidine compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Life Science Amino Acids and their Derivatives Proline and derivatives

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Amino Acid Derivatives

Key Words

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(4R)-1-Fmoc-4-(allyloxycarbonylamino)-L-proline

CAS No. 273222-05-2

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