Z-Trp-OMe

Name: Z-Trp-OMe
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 2717-76-2
Cat. No. CS-0150965
Purity≥98%
MDL No.MFCD06658545

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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 2717-76-2

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General Information

CAS No. 2717-76-2
Cat. No. CS-0150965
Purity ≥98%
MDL No. MFCD06658545
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₀H₂₀N₂O₄
Molecular Weight 352.38
Synonym(s) (S)-methyl 2-(benzyloxycarbonylamino)-3-(1H-indol-3-yl)propanoate
SMILES COC([C@@H](NC(OCC1=CC=CC=C1)=O)CC2=CNC3=CC=CC=C23)=O

Description

Z-Trp-OMe features a protected tryptophan side chain with a benzoyloxycarbonyl (Z) group and methyl ester functionality, enabling stable incorporation into peptide synthesis. The Z group provides steric shielding and enhanced solubility during coupling steps, while the OMe ester simplifies downstream deprotection. This derivative facilitates efficient access to C-terminal modified peptides under standard conditions.

Application

Z-Trp-OMe serves as a robust building block for peptide synthesis, offering the indole side chain of tryptophan in a protected form. The benzyloxycarbonyl (Z) group ensures stability during coupling steps, while the methyl ester facilitates downstream transformations. It enables efficient incorporation into linear and cyclic peptides, with excellent compatibility in standard Fmoc and Boc protocols.

Synthesis

Route1
- 67-56-1
- In-stock
  
  7432-21-5
- ~99%
- In-stock
  
  2717-76-2
References
- Ley, Steven V.; Cleator, Ed; Hewitt, Peter R. Organic and Biomolecular Chemistry, 2003 , vol. 1, # 20 p. 3492 - 3494
Route2
- In-stock
  
  7524-52-9
- 501-53-1
- ~99%
- In-stock
  
  2717-76-2
References
- Yoshioka, Tadao; Mohri, Kunihiko; Oikawa, Yuji; Yonemitsu, Osamu Journal of Chemical Research, Miniprint, 1981 , # 7 p. 2252 - 2281
Route3
- 1053208-94-8
- ~87%
- In-stock
  
  2717-76-2
References
- Coste, Alexis; Toumi, Mathieu; Wright, Karen; Razafimahaleo, Vanessa; Couty, Francois; Marrot, Jerome; Evano, Gwilherm Organic Letters, 2008 , vol. 10, # 17 p. 3841 - 3844

Safety Information

Download SDS

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 80.42
LogP 3.1784
H_Acceptors 4
H_Donors 2
Rotatable_Bonds 6

Other Classifications

Building Blocks Functional Group Ester

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Aromatic heterocycle compounds Indole compounds

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

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CAS No. 2717-76-2

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