Z-Asp(OtBu)-OH

Name: Z-Asp(OtBu)-OH
Brand: ChemScene
Availability: InStock
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CAS No. 5545-52-8
Cat. No. CS-W011994
Purity≥98%
MDL No.MFCD00042857

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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 5545-52-8

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General Information

CAS No. 5545-52-8
Cat. No. CS-W011994
Purity ≥98%
MDL No. MFCD00042857
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₆H₂₁NO₆
Molecular Weight 323.34
Synonym(s) None
SMILES CC(C)(C)OC(C[C@@H](C(O)=O)NC(OCC1=CC=CC=C1)=O)=O

Description

Z-Asp(OtBu)-OH is a protected aspartic acid derivative featuring a benzyloxycarbonyl (Z) group at the α-amino position and a tert-butyl ester at the side-chain carboxyl. This configuration enables stable incorporation into peptide chains under standard coupling conditions, with orthogonal deprotection compatibility for sequential synthesis. The Z group facilitates purification and handling during solid-phase peptide synthesis workflows.

Application

Z-Asp(OtBu)-OH serves as a key dipeptide building block in peptide synthesis, enabling efficient formation of C-terminal protected aspartic acid residues. The Z (benzyloxycarbonyl) group provides stable N-protection, while the OtBu (tert-butyl ester) offers orthogonal protection for the side-chain carboxylate. This combination facilitates selective coupling reactions, excellent bench stability, and straightforward deprotection under standard conditions, making it ideal for the synthesis of complex peptide sequences and peptidomimetics.

Synthesis

Route1
- 63327-57-1
- ~89%
- In-stock
  
  5545-52-8
References
- Nuijens, Timo; Kruijtzer, John A.W.; Cusan, Claudia; Rijkers, Dirk T.S.; Liskamp, Rob M.J.; Quaedflieg, Peter J.L.M. Tetrahedron Letters, 2009 , vol. 50, # 23 p. 2719 - 2721
Route2
- 23632-69-1
- ~81%
- In-stock
  
  5545-52-8
References
- Chevallet, Pierre; Garrouste, Patrick; Malawska, Barbara; Martinez, Jean Tetrahedron Letters, 1993 , vol. 34, # 46 p. 7409 - 7412
Route3
- 540-88-5
- In-stock
  
  1152-61-0
- ~0%
- In-stock
  
  47307-26-6
- In-stock
  
  5545-52-8
- 42417-76-5
References
- Allen, David Robert; Kyung-Lee, Seung-Hee Patent: US2003/236430 A1, 2003 ; Location in patent: Page 3 ;

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 101.93
LogP 2.0978
H_Acceptors 5
H_Donors 2
Rotatable_Bonds 6

Other Classifications

Bioactive Molecules Peptides

Life Science Amino Acids and their Derivatives Aspartic acid and derivatives

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Amino Acid Derivatives

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

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

Biochemistry Biochemicals and Reagents Amino Acids N-Protected Amino Acids

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Z-Asp(OtBu)-OH

CAS No. 5545-52-8

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