(S)-1-((S)-2-((tert-Butoxycarbonyl)amino)propanoyl)pyrrolidine-2-carboxylic acid

Name: (S)-1-((S)-2-((tert-Butoxycarbonyl)amino)propanoyl)pyrrolidine-2-carboxylic acid
Brand: ChemScene
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CAS No. 33300-72-0
Cat. No. CS-0158180
Purity≥97%
MDL No.None

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(S)-1-((S)-2-((tert-Butoxycarbonyl)amino)propanoyl)pyrrolidine-2-carboxylic acid|CS-0158180

Structure of 33300-72-0

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General Information

CAS No. 33300-72-0
Cat. No. CS-0158180
Purity ≥97%
MDL No. None
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₂₂N₂O₅
Molecular Weight 286.32
Synonym(s) N-(tert-butoxycarbonyl)alanylproline
SMILES C[C@H](NC(OC(C)(C)C)=O)C(N1CCC[C@H]1C(O)=O)=O

Description

(S)-1-((S)-2-((tert-Butoxycarbonyl)amino)propanoyl)pyrrolidine-2-carboxylic acid features a stereochemically defined pyrrolidine core with a protected amino acid side chain, enabling direct incorporation into peptide sequences. The tert-butoxycarbonyl group ensures stability during synthesis and facilitates selective deprotection. This configuration supports efficient coupling in solid-phase peptide synthesis workflows.

Application

(S)-1-((S)-2-((tert-Butoxycarbonyl)amino)propanoyl)pyrrolidine-2-carboxylic acid serves as a versatile chiral building block for the synthesis of peptidomimetics and cyclic peptide scaffolds. Its rigid pyrrolidine core, combined with orthogonal protection (Boc on amine, carboxylic acid), enables selective functionalization and efficient coupling in solid-phase and solution-phase syntheses. The molecule exhibits excellent bench stability and facilitates purification via standard chromatographic methods, making it well-suited for medicinal chemistry campaigns requiring stereocontrolled construction of bioactive architectures.

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-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 95.94
LogP 0.9752
H_Acceptors 4
H_Donors 2
Rotatable_Bonds 3

Other Classifications

Building Blocks Functional Group Boc

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Aliphatic heterocycle compounds Pyrrolidine compounds

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

Key Words

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(S)-1-((S)-2-((tert-Butoxycarbonyl)amino)propanoyl)pyrrolidine-2-carboxylic acid

CAS No. 33300-72-0

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