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H6875

Sigma-Aldrich

Hippuryl-L-phenylalanine

Synonym(s):

Hippuryl-Phe, N-Benzoyl-Gly-Phe

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About This Item

Empirical Formula (Hill Notation):
C18H18N2O4
CAS Number:
744-59-2
Molecular Weight:
326.35
Beilstein/REAXYS Number:
2167818
EC Number:
212-016-7
MDL number:
MFCD00037265
UNSPSC Code:
12352204
PubChem Substance ID:
24895770
NACRES:
NA.32

assay

≥98% (TLC)

form

powder

solubility

acetic acid: 50 mg/mL, clear, colorless

storage temp.

−20°C

SMILES string

OC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)c2ccccc2

InChI

1S/C18H18N2O4/c21-16(12-19-17(22)14-9-5-2-6-10-14)20-15(18(23)24)11-13-7-3-1-4-8-13/h1-10,15H,11-12H2,(H,19,22)(H,20,21)(H,23,24)/t15-/m0/s1

InChI key

CCLJGZGVIQBNDH-HNNXBMFYSA-N

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Application

Hippuryl-L-phenylalanine has been used as a substrate for screening carboxypeptidase activity in Trogoderma granarium, Bactrocera oleae Gmelin and Apodiphus amygdali.

Biochem/physiol Actions

Hippuryl-L-phenylalanine is a substrate for carboxypeptidase A enzyme.

Substrates

Substrate for carboxypeptidase A

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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Product stabilization of the two forms of carboxypeptidase A from buffalo pancreas
Sud M and Dua RD
Journal of Biosciences, 9(1-2), 83-90 (1985)
J H Cho et al.
Biochemistry, 40(34), 10197-10203 (2001-08-22)
We have investigated the function of Tyr248 using bovine wild-type CPA and its Y248F and Y248A mutants to find that the K(M) values were increased by 4.5-11-fold and the k(cat) values were reduced by 4.5-10.7-fold by the replacement of Tyr248
Digestion and protein metabolism of Trogoderma granarium (Coleoptera: Dermestidae) fed on different barley varieties
Mardani-Talaee M, et al.
Journal of Stored Products Research, 73(1-2), 37-41 (2017)
E Normant et al.
Neuropeptides, 30(1), 13-17 (1996-02-01)
We have designed two radioactive substrates, hippuryl-L-[3H]phenylalanine and 3-(p-hydroxy, m-[125I]phenyl)propionic acid ([125I]Bolton reagent) derivative of L-arginyl-L-phenylalanine, i.e. [125I]BRF, for a highly sensitive assay of carboxypeptidase A (CPA) activity. After cleavage of the C-terminal phenylalanine residue by CPA, the radioactive product
J F Sebastian et al.
Canadian journal of biochemistry, 56(5), 329-333 (1978-05-01)
3,3-Diphenylpropanoate (DPP) activates the carboxypeptidase A catalyzed hydrolysis of benzoylglycyl-L-phenylalanine (BzGly-L-Phe) (Ka = 2.1 x 10 (-3) M) and inhibits ester hydrolysis uncompetitively (K1 =2.1 X 10 (-3) M). A common modifier binding site located adjacent to the peptide and
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Protocols

Enzymatic Assay: Carboxypeptidase

Carboxypeptidase A activity measured via continuous spectrophotometric rate determination assay with hippuryl-L-phenylalanine substrate.

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