(2S,4S)-4-((tert-Butoxycarbonyl)amino)pyrrolidine-2-carboxylic acid

Name: (2S,4S)-4-((tert-Butoxycarbonyl)amino)pyrrolidine-2-carboxylic acid
Brand: ChemScene
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CAS No. 1279034-78-4
Cat. No. CS-0112833
Purity≥98%
MDL No.MFCD08704525

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(2S,4S)-4-((tert-Butoxycarbonyl)amino)pyrrolidine-2-carboxylic acid|CS-0112833

Structure of 1279034-78-4

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Description

This chiral pyrrolidine derivative features a protected amine and carboxylic acid group, enabling direct incorporation into peptide synthesis. The tert-butoxycarbonyl (Boc) group ensures stability during coupling steps, while the (2S,4S) stereochemistry provides defined spatial orientation for constrained peptide backbones. This scaffold delivers high diastereoselectivity in macrocyclization reactions and maintains integrity under standard bench conditions.

Application

(2S,4S)-4-((tert-Butoxycarbonyl)amino)pyrrolidine-2-carboxylic acid serves as a stereochemically defined building block for the synthesis of peptidomimetics and bioactive heterocycles. The Boc-protected amine enables straightforward coupling reactions with carboxylic acids or alcohols, while the pyrrolidine scaffold provides conformational rigidity and enhanced metabolic stability. Its bench-stable nature and compatibility with standard peptide synthesis protocols facilitate efficient incorporation into complex molecular architectures.

General Information

CAS No. 1279034-78-4
Cat. No. CS-0112833
Purity ≥98%
MDL No. MFCD08704525
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₀H₁₈N₂O₄
Molecular Weight 230.26
Synonym(s) (4S)-4-[[(1,1-Dimethylethoxy)carbonyl]amino]-L-proline
SMILES O=C([C@H]1NC[C@@H](NC(OC(C)(C)C)=O)C1)O

Computational Chemistry Data

TPSA 87.66
LogP 0.3262
H_Acceptors 4
H_Donors 3
Rotatable_Bonds 2

Safety Information

Download SDS

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

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Other Classifications

Building Blocks Functional Group Carboxylic Acid

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 Unnatural Amino Acid Derivatives

Key Words

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(2S,4S)-4-((tert-Butoxycarbonyl)amino)pyrrolidine-2-carboxylic acid

CAS No. 1279034-78-4

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