15386

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
Linear Formula:
C6H5CH2OCOCH2CH(COOH)NHCOOC(CH3)3
CAS Number:
Molecular Weight:
323.34
Beilstein/REAXYS Number:
2064127
EC Number:
MDL number:
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

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

application(s)

peptide synthesis: suitable

mp

98-102 °C (lit.)

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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Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
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...
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)
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...
Articles
With a growing peptide drug market the fast, reliable and uncomplicated synthesis of peptides is of paramount importance.
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