3401-36-3

Basic information

• Product Name: Z-ALA-OSU
• Synonyms: N-CARBOBENZOXY-L-ALANINE-N-HYDROXYSUCCINIMIDE ESTER;Z-L-ALANINE-N-HYDROXYSUCCINIMIDE ESTER;Z-L-ALANINE HYDROXYSUCCINIMIDE ESTER;Z-ALANINE-OSU;Z-ALA-OSU;CBZ-L-ALANINE HYDROXYSUCCINIMIDE ESTER;BENZYLOXYCARBONYL-L-ALANINE N-HYDROXYSUCCINIMIDE ESTER;CBZ-L-ALANINE N-SUCCINIMIDE ESTER
• CAS NO: 3401-36-3
• Molecular Formula: C₁₅H₁₆N₂O₆
• Molecular Weight: 320.3
• EINECS: 1533716-785-6
• Product Categories: Amino Acid Derivatives
• Mol File: 3401-36-3.mol
• Article Data: 27

Chemical Properties

• Melting Point: 119-123 °C
• Appearance: /
• Density: 1.36 g/cm³
• Refractive Index: 1.579
• Storage Temp.: −20°C
• CAS DataBase Reference: Z-ALA-OSU(CAS DataBase Reference)
• NIST Chemistry Reference: Z-ALA-OSU(3401-36-3)
• EPA Substance Registry System: Z-ALA-OSU(3401-36-3)

Safety Data

• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 3401-36-3(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white powder

InChI:InChI=1/C15H16N2O6/c1-10(14(20)23-17-12(18)7-8-13(17)19)16-15(21)22-9-11-5-3-2-4-6-11/h2-6,10H,7-9H2,1H3,(H,16,21)/t10-/m0/s1

Upstream product

• 1142-20-7 N-Cbz-Ala 
• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 1142-20-7 N-benzyloxycarbonyl-L-alanine 
• 74124-79-1 di(succinimido) carbonate 
• 501-53-1 benzyl chloroformate 
• 90704-86-2 bis(N-hydroxysuccinimide) sulfite 
• 107960-02-1 1,2,2,2-tetrachloroethyl-(N-succinimidyl)carbonate 
• 57296-03-4 N,N’-disuccinimidyl oxalate 
• 75513-55-2 N-hydroxysuccinimido diphenyl phosphate 

Downstream Products

• 102096-27-5 [(S)-1-(6-Methoxy-quinolin-8-ylcarbamoyl)-ethyl]-carbamic acid benzyl ester 
• 27255-42-1 N,N'-Bis-(N-benzyloxycarbonyl-L-alanyl)-ethylendiamin 
• 83852-28-2 N,N'-bis(N-(carbobenzyloxy)-L-phenylalanyl)-1,3-diaminopropane 
• 2503-31-3 N-benzyloxycarbonyl-L-alanylglycine 
• 184849-25-0 ((S)-1-{2-[2-((S)-2-Benzyloxycarbonylamino-propionylamino)-ethylamino]-ethylcarbamoyl}-ethyl)-carbamic acid benzyl ester 
• 213528-68-8 [(S)-1-((2S,3R,4R,5S,6R)-2-Allyloxy-6-azidomethyl-4,5-dihydroxy-tetrahydro-pyran-3-ylcarbamoyl)-ethyl]-carbamic acid benzyl ester 
• 871579-12-3 (S)-N-benzyloxycarbonyl-N'-(4-cyanophenyl)alaninamide 
• 3408-50-2 [(N-benzyloxycarbonyl)-L-alaninyl]-L-aspartic acid [beta]-tert-butyl ester 
• 875556-82-4 (R)-2-((S)-2-Benzyloxycarbonylamino-propionylamino)-3-bromo-propionic acid methyl ester 
• 957148-23-1 C₁₄H₂₂N₄O₂ 
• 84437-90-1 N-benzyloxycarbonyl-L-alanyldehydroalanine benzyl ester 
• 161007-06-3 Z-L-Ala-α-AeMet(γ-Phth)-L-Ala-OtBu 
• 144232-73-5 N-benzyloxycarbonyl-L-alanyl-L-argininal dibutylacetal hydrochloride 
• 21027-01-0 N-benzyloxycarbonyl-L-alanyl-L-proline 

Relevant articles and documents

Ynamide-Mediated Thiopeptide Synthesis

Exploration of the full potential of thioamide substitution as a tool in the chemical biology of peptides and proteins has been hampered by insufficient synthetic strategies for the site-specific introduction of a thioamide bond into a peptide backbone. A novel ynamide-mediated two-step strategy for thiopeptide bond formation with readily available monothiocarboxylic acids as thioacyl donors is described. The α-thioacyloxyenamide intermediates formed from the ynamides and monothiocarboxylic acids can be purified, characterized, and stored. The balance between their activity and stability enables them to act as effective thioacylating reagents to afford thiopeptide bonds under mild reaction conditions. Amino acid functional groups such as OH, CONH2, and indole NH groups need not be protected during thiopeptide synthesis. The modular nature of this strategy enables the site-specific incorporation of a thioamide bond into peptide backbones in both solution and the solid phase.

An efficient procedure for the preparation of carboxamides and peptides using in situ generated N-succinimidyl active esters

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C2 symmetrical nickel complexes derived from α-amino amides as efficient catalysts for the enantioselective addition of dialkylzinc reagents to aldehydes

A series of C2 symmetrical 1:2 Ni:L complexes derived from α-amino amides were studied for the enantioselective addition of dialkylzinc reagents to aldehydes. Different structural elements on the ligands seem to play an important role in determining the observed enantioselectivity. Through optimization of structure and reaction conditions, the best ligand provided secondary alcohols in excellent yields (up to 98%) and enantioselectivity of up to 99% ee for (R)-enantiomer. A transition state model has been proposed to explain the observed enantioselectivities based on computational calculations at the DFT level. Very interestingly, calculations suggest a coordination model of the aldehyde to the metal complex through association of a lone pair of the carbonyl oxygen to the hydrogen atom of an amino group.