N-Fmoc-3-iodo-L-alanine methyl ester

Name: N-Fmoc-3-iodo-L-alanine methyl ester
Brand: ChemScene
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CAS No. 156017-42-4
Cat. No. CS-0356399
Purity≥97%
MDL No.MFCD13189980

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Excepted Quantity	$0.00
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N-Fmoc-3-iodo-L-alanine methyl ester|CS-0356399

Structure of 156017-42-4

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General Information

CAS No. 156017-42-4
Cat. No. CS-0356399
Purity ≥97%
MDL No. MFCD13189980
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₉H₁₈INO₄
Molecular Weight 451.25
Synonym(s) None
SMILES COC([C@H](CI)NC(OCC1C2=CC=CC=C2C3=CC=CC=C31)=O)=O

Description

N-Fmoc-3-iodo-L-alanine methyl ester features a bench-stable Fmoc protecting group and a reactive iodine substituent at the C3 position, enabling direct late-stage functionalization in peptide synthesis. This electrophilic handle facilitates efficient palladium-catalyzed coupling reactions, streamlining access to non-natural amino acid derivatives for chemical biology and drug discovery applications.

Application

N-Fmoc-3-iodo-L-alanine methyl ester serves as a versatile building block for the synthesis of iodinated amino acid derivatives and peptide conjugates. The Fmoc group enables orthogonal protection in solid-phase peptide synthesis, while the iodine substituent at C3 facilitates late-stage functionalization via palladium-catalyzed cross-coupling reactions. Its methyl ester functionality supports straightforward derivatization and purification, offering excellent bench stability and compatibility with standard synthetic workflows.

Synthesis

Route1
- 229962-91-8
- ~89%
- In-stock
  
  156017-42-4
References
- Tabanella, Stefania; Valancogne, Ingrid; Jackson, Richard F W Organic and biomolecular chemistry, 2003 , vol. 1, # 23 p. 4254 - 4261
Route2
- In-stock
  
  82911-78-2
- ~%
- In-stock
  
  156017-42-4
References
- Smyth; Burke Jr. Tetrahedron Letters, 1994 , vol. 35, # 4 p. 551 - 554
Route3
- In-stock
  
  82911-69-1
- ~%
- In-stock
  
  156017-42-4
References
- Shao, Hui; Lockman, Jeffrey W.; Parquette, Jon R. Journal of the American Chemical Society, 2007 , vol. 129, # 7 p. 1884 - 1885

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-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 64.63
LogP 3.5017
H_Acceptors 4
H_Donors 1
Rotatable_Bonds 5

Other Classifications

Building Blocks Functional Group Fmoc

Building Blocks Functional Group Iodide

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

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N-Fmoc-3-iodo-L-alanine methyl ester

CAS No. 156017-42-4

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