1-Adamantylaspartate
Basic information
- CAS
115545-59-0- Standard SMILES
N[C@@H](CC(=O)OC12CC3CC(CC(C3)C1)C2)C(=O)O- InChIKey
JWPBQLVAJXYMGD-RLFZITJJSA-N- Molecular formula
- C14H21NO4
- Average molar mass
- 267.32 g/mol
- Monoisotopic mass
- 267.14705815
Overview
useful as a protecting group for protein synthesis; structure given in first source
Names & identifiers
- Preferred name
- 1-Adamantylaspartate
- IUPAC
- (2S)-4-(1-adamantyloxy)-2-amino-4-oxobutanoic acid
- English name
- 1-adamantylaspartate
- Molecular formula
- C14H21NO4
- Molecular weight
- 267.32
Names & synonyms
1-Adamantylaspartate115545-59-0H-Asp(O-1-ada)-OHbeta-1-Adamantylaspartic acidRefChem:74831(2S)-4-(1-adamantyloxy)-2-amino-4-oxobutanoic acidL-Aspartic acid, 4-tricyclo(3.3.1.13,7)dec-1-yl esterorb1698874SCHEMBL9794643(S)-4-(Adamantan-1-yloxy)-2-amino-4-oxobutanoic acidAKOS030606752HY-118161
Show more names
1Adamantylaspartate,1 AdamantylaspartateL-Aspartic acid, 4-tricyclo[3.3.1.13,7]dec-1-yl ester
T29295
Database identifiers
- CAS
115545-59-0- PubChem CID
- 64585
Properties
Computed structural properties
- XLogP
- -0.9
- Topological polar surface area
- 89.6 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 5
- Heavy atoms
- 19
- Formal charge
- 0
- Complexity
- 365
Physicochemical properties
- Melting point
- 240 °C · 240 °C (decomp)
- Boiling point
- 439.8 · 439.8±40.0 °C(Predicted)
- Density
- 1.28 · 1.28±0.1 g/cm3(Predicted)
- pka
- 2.19 · 2.19±0.23(Predicted)
Chemistry & industry
Applications
Uses1-Adamantylaspartate is a newly developed β-β-1-imidopropionic acid used to synthesize the C-terminal octapeptide of the β subunit of human chorionic gonadotropin (hCG) and the hexadecapeptide of the α subunit of the insulin receptor (30-55) by conventional solution methods and solid phase methods, aiming to inhibit the formation of asparagine during the synthesis of asparagyl peptides. Studies have shown that β-β-1-imidopropionic acid is an effective protector of the β-carboxyl function of aspartic acid residues.
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