(4S)-4-Hydroxy-D-proline

Name: (4S)-4-Hydroxy-D-proline
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 3398-22-9
Cat. No. CS-0020162
Purity≥97%
MDL No.MFCD00065608

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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+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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Structure of 3398-22-9

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General Information

CAS No. 3398-22-9
Cat. No. CS-0020162
Purity ≥97%
MDL No. MFCD00065608
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₅H₉NO₃
Molecular Weight 131.13
Synonym(s) None
SMILES OC([C@H]1C[C@@H](CN1)O)=O

Description

trans-D-4-Hydroxyproline features a stable trans-configured pyrrolidine ring with a hydroxyl group at the C4 position, conferring enhanced rigidity and conformational control. This stereochemical configuration promotes precise secondary structure induction in peptide scaffolds, making it essential for stabilizing collagen-like motifs in synthetic biomolecules and bioactive peptides under physiological conditions.

Application

trans-D-4-Hydroxyproline serves as a key building block in the synthesis of collagen-mimetic peptides and proline-rich bioactive molecules. Its stable trans configuration and well-defined stereochemistry enable reliable incorporation into peptide sequences, facilitating structural studies and medicinal chemistry campaigns. The hydroxyl group offers a handle for further derivatization, while its bench-stable nature supports straightforward handling and purification in standard synthetic workflows.

Synthesis

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References
- Journal of Biological Chemistry, , vol. 204, p. 307,313 Journal of Biological Chemistry, , vol. 195, p. 383,384
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References
- Journal of Biological Chemistry, , vol. 195, p. 383,384
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  3398-22-9
References
- Acta Physica et Chemica, , vol. 3, p. 118

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07,GHS08
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H334-H335
Precautionary Statements : P261-P264-P270-P271-P280-P284-P302+P352-P304+P340-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 69.56
LogP -1.2062
H_Acceptors 3
H_Donors 3
Rotatable_Bonds 1

Other Classifications

Bioactive Molecules Dye and Bio-assay Reagents

Life Science Amino Acids and their Derivatives Proline and derivatives

Building Blocks Functional Group Alcohol

Building Blocks Functional Group Carboxylic Acid

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Aliphatic heterocycle compounds Pyrrolidine compounds

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

Chemical Biology Pharmaceutical Development and Drug Discovery Research Reagents Peptide Chemistry Unnatural Amino Acid Derivatives

Chemical Biology Pharmaceutical Development and Drug Discovery Research Peptide Chemistry Amino Acid Derivatives

Chemical Biology Pharmaceutical Development and Drug Discovery Research Peptide Chemistry Unnatural Amino Acid Derivatives

Key Words

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(4S)-4-Hydroxy-D-proline

CAS No. 3398-22-9

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