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Sigma-Aldrich

Boc-Asp(OBzl)-OH

≥99.0% (sum of enantiomers, HPLC)

Synonym(s):

N-(tert-Butoxycarbonyl)-L-aspartic acid 4-benzyl ester, Boc-L-aspartic acid 4-benzyl ester

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About This Item

Linear Formula:
C6H5CH2OCOCH2CH(COOH)NHCOOC(CH3)3
CAS Number:
7536-58-5
Molecular Weight:
323.34
Beilstein/REAXYS Number:
2064127
EC Number:
231-406-8
MDL number:
MFCD00065564
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
57647403
NACRES:
NA.22

assay

≥99.0% (sum of enantiomers, HPLC)

optical activity

[α]20/D −20.0±1°, c = 2% in DMF

reaction suitability

reaction type: Boc solid-phase peptide synthesis

mp

98-102 °C (lit.)

application(s)

peptide synthesis

SMILES string

[H][C@@](CC(=O)OCc1ccccc1)(NC(=O)OC(C)(C)C)C(O)=O

InChI

1S/C16H21NO6/c1-16(2,3)23-15(21)17-12(14(19)20)9-13(18)22-10-11-7-5-4-6-8-11/h4-8,12H,9-10H2,1-3H3,(H,17,21)(H,19,20)/t12-/m0/s1

InChI key

SOHLZANWVLCPHK-LBPRGKRZSA-N

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Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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Vitamin K1 dependent carboxylase: beta-carboxylation of t-butyloxycarbonylaspartic acid alpha-benzyl ester.
S E Hamilton et al.
Biochemical and biophysical research communications, 107(1), 246-249 (1982-07-16)
Nicole Niklas et al.
Dalton transactions (Cambridge, England : 2003), (1)(1), 154-162 (2006-12-13)
The amino acid derivative Boc-Asp-OBzl (Boc=N-butyloxycarbonyl; Asp=aspartic acid; Bzl=benzyl) was functionalized by coupling its carboxylate side chain to dipicolylamine. This yielded the tridentate nitrogen donor ligand Boc-Asp(Dpa)-OBzl (-OBzl). The compound -OBzl contains three different carbonyl groups: a tertiary amide linkage
J J McTigue et al.
The Journal of biological chemistry, 259(7), 4272-4278 (1984-04-10)
The rat liver microsomal vitamin K-dependent carboxylase has been shown to carboxylate the aspartyl residue in N alpha-t-butyloxycarbonylaspartic acid alpha-benzyl ester to a beta-carboxyaspartyl residue. The enzyme also carboxylates aspartyl residues in low molecular weight peptides to beta-carboxyaspartyl residues, but
Tomohisa Sawada et al.
Nature communications, 10(1), 5687-5687 (2019-12-14)
Cavity creation is a key to the origin of biological functions. Small cavities such as enzyme pockets are created simply through liner peptide folding. Nature can create much larger cavities by threading and entangling large peptide rings, as learned from

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