Nα-Z-L-asparagine tert-butyl ester
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Nα-Z-L-asparagine tert-butyl ester

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Category
CBZ-Amino Acids
Catalog number
BAT-003223
CAS number
25456-85-3
Molecular Formula
C16H22N2O5
Molecular Weight
322.36
Nα-Z-L-asparagine tert-butyl ester
IUPAC Name
tert-butyl (2S)-4-amino-4-oxo-2-(phenylmethoxycarbonylamino)butanoate
Synonyms
Z-L-Asn-OtBu; tert-butyl (2S)-4-amino-4-oxo-2-(phenylmethoxycarbonylamino)butanoate
Appearance
White powder
Purity
99%
Density
1.188±0.06 g/cm3(Predicted)
Melting Point
105-107 °C
Boiling Point
542.0±50.0 °C(Predicted)
Storage
Store at 2-8 °C
InChI
InChI=1S/C16H22N2O5/c1-16(2,3)23-14(20)12(9-13(17)19)18-15(21)22-10-11-7-5-4-6-8-11/h4-8,12H,9-10H2,1-3H3,(H2,17,19)(H,18,21)/t12-/m0/s1
InChI Key
CHLOOSRSKMKBDP-LBPRGKRZSA-N
Canonical SMILES
CC(C)(C)OC(=O)C(CC(=O)N)NC(=O)OCC1=CC=CC=C1

Nα-Z-L-asparagine tert-butyl ester, a versatile peptide synthesis reagent and protective group, finds extensive usage in organic and medicinal chemistry. Here are the key applications presented with heightened perplexity and burstiness:

Peptide Synthesis: Widely embraced in peptide synthesis, Nα-Z-L-asparagine tert-butyl ester serves as a pivotal protective group, safeguarding amino acid functional groups during peptide elongation. This protective shield prevents undesirable side reactions, facilitating the generation of high-purity peptides crucial for advancing pharmaceutical research and therapeutic innovation.

Organic Synthesis: Within the realm of organic chemistry, Nα-Z-L-asparagine tert-butyl ester emerges as an indispensable intermediate in crafting intricate molecules. Selectively removable under mild conditions, its protective group empowers chemists to construct multifunctional compounds with efficiency. This capability fosters the development of diverse chemical entities spanning applications from materials science to medicinal chemistry.

Drug Development: Unveiling new horizons in pharmaceutical advancements, researchers harness Nα-Z-L-asparagine tert-butyl ester in designing peptide-based drugs. This reagent allows for precise integration of asparagine residues into peptide chains, a critical factor influencing biological activity and drug stability. Instrumental in crafting potential therapies for diverse ailments such as cancer and infectious diseases, this compound stands at the forefront of drug innovation.

Bioconjugation: Elevating bioconjugation techniques to new heights, Nα-Z-L-asparagine tert-butyl ester plays a vital role in linking peptides with other biomolecules like proteins or antibodies. By safeguarding the integrity of the asparagine residue during conjugation, it ensures the functional coherence of the peptide. This application is pivotal in shaping targeted therapies, diagnostics, and cutting-edge biotechnological tools.

1. Phenyl 3,5-di-tert-butyl-2-hy-droxy-benzoate
Alexander Carreño, Marcelo Preite, Juan Manuel Manriquez, Andrés Vega, Ivonne Chavez Acta Crystallogr Sect E Struct Rep Online. 2010 Nov 24;66(Pt 12):o3290. doi: 10.1107/S1600536810044028.
The title mol-ecule, C(21)H(26)O(3), has a six-membered planar carbon ring as the central core, substituted at position 1 with phen-oxy-carbonyl, at position 2 with hy-droxy and at positions 3 and 5 with tert-butyl groups. The structure shows two independent but very similar mol-ecules within the asymmetric unit. For both independent mol-ecules, the ester carboxyl-ate group is coplanar with the central core, as reflected by the small C-C-O-C torsion angles [179.95 (17) and 173.70 (17)°]. In contrast, the phenyl substituent is almost perpendicular to the carboxyl-ate -CO(2) fragment, as reflected by C-O-C-C torsion angles, ranging from 74 to 80°. The coplanarity between the central aromatic ring and the ester carboxyl-ate -CO(2)- group allows the formation of an intra-molecular hydrogen bond, with O⋯O distances of 2.563 (2) and 2.604 (2) Å.
2. Di-tert-butyl (2R,3R)-2-{[(2E)-3-(4-acet-yloxy-3-meth-oxy-phen-yl)prop-2-eno-yl]-oxy}-3-hy-droxy-butane-dioate
Josh L Hixson, Dennis K Taylor, Seik Weng Ng, Edward R T Tiekink Acta Crystallogr Sect E Struct Rep Online. 2012 Mar 1;68(Pt 3):o568-9. doi: 10.1107/S1600536812002784. Epub 2012 Feb 4.
In the title mol-ecule, C(24)H(32)O(10), one tert-butyl ester group is folded towards the central benzene ring while the other is directed away. The acetyl group is almost perpendicular to the benzene ring to which it is connected [C-C-O-C torsion angle = 90.4 (12)°]. The conformation about the ethene bond [1.313 (7) Å] is E. The atoms of the benzene ring and its attached ester group and part of the hy-droxy tert-butyl ester side chain are disordered over two sets of sites in a 50:50 ratio. Linear supra-molecular chains along the a axis mediated by hy-droxy-carbonyl O-H⋯O hydrogen bonds feature in the crystal packing. The same H atom also partakes in an intra-molecular O-H⋯O inter-action.
3. The peptide Z-Aib-Aib-Aib-L-Ala-OtBu
Renate Gessmann, Hans Brückner, Kyriacos Petratos Acta Crystallogr C Struct Chem. 2014 Apr;70(Pt 4):405-7. doi: 10.1107/S2053229614005567. Epub 2014 Mar 21.
The title peptide, N-benzyloxycarbonyl-α-aminoisobutyryl-α-aminoisobutyryl-α-aminoisobutyryl-L-alanine tert-butyl ester or Z-Aib-Aib-Aib-L-Ala-OtBu (Aib is α-aminoisobutyric acid, Z is benzyloxycarbonyl and OtBu indicates the tert-butyl ester), C27H42N4O7, is a left-handed helix with a right-handed conformation in the fourth residue, which is the only chiral residue. There are two 4→1 intramolecular hydrogen bonds in the structure. In the lattice, molecules are hydrogen bonded to form columns along the c axis.
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