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A9075

Sigma-Aldrich

(2S,3R)-3-Amino-2-hydroxy-4-phenylbutyric acid hydrochloride

Synonym(e):

(2S,3R)-AHPA

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About This Item

Empirische Formel (Hill-System):
C10H13NO3 · HCl
CAS-Nummer:
128223-55-2
Molekulargewicht:
231.68
MDL-Nummer:
MFCD00274394
UNSPSC-Code:
12352200
PubChem Substanz-ID:
24891224

Form

solid

Lagertemp.

−20°C

SMILES String

Cl.N[C@H](Cc1ccccc1)[C@H](O)C(O)=O

InChI

1S/C10H13NO3.ClH/c11-8(9(12)10(13)14)6-7-4-2-1-3-5-7;/h1-5,8-9,12H,6,11H2,(H,13,14);1H/t8-,9+;/m1./s1

InChIKey

OPVMPYQFOLATCK-RJUBDTSPSA-N

Biochem./physiol. Wirkung

(2S,3R)-3-Amino-2-hydroxy-4-phenylbutyric acid (AHPA) derivatives are used as inhibitors of enkephalinase(s) to augment met5-enkephalin-induced anti-nociception. The derivative (2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl-L-valine (AHPA-Val) is used as a bestatin analogue.

Piktogramme

Exclamation mark
GHS07

Signalwort

Warning

Gefahreneinstufungen

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Zielorgane

Respiratory system

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves

Analysenzertifikate (COA)

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F Abe et al.
The Journal of antibiotics, 41(12), 1862-1867 (1988-12-01)
The biological activity of the two main metabolites of ubenimex in humans, (-)-N-[(2S,3R)-3-amino-2-hydroxy-4-(4'-hydroxy)phenylbutyryl]-L-leucine (OH-ubenimex) and (2S,3R)-3-amino-2-hydroxy-4-phenylbutyric acid [2S,3R)-AHPA) was examined. OH-Ubenimex was almost identical in inhibitory activity against mouse peritoneal resident macrophage aminopeptidases (APases) and the growth of IMC carcinoma
Y Matsuoka et al.
Japanese journal of pharmacology, 46(3), 205-210 (1988-03-01)
It has been accepted that the periaqueductal gray matter of the mid brain (PAG) and the reticular formation of the medulla oblongata in the brain stem have antinociceptive roles in the pain control pathways of mammals, and met5-enkephalin may act
M Hachisu et al.
Life sciences, 30(20), 1739-1746 (1982-05-17)
The effects of nineteen AHPA* derivatives were examined on morphine analgesia by tail-flick test in rats and on enkephalinase inhibition which was based on the formation of tyrosyl-glycyl-glycine from met-enkephalin. The correlation between the enhancement of morphine analgesia in vivo
M C Chung et al.
Bioscience, biotechnology, and biochemistry, 60(5), 898-900 (1996-05-01)
A bestatin analogue, (2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl-L-valine (AHPA-Val), from the culture filtrate of Streptomyces neyagawaensis SL-387 was obtained in a chemically defined medium containing DL-3-amino-3-phenylpropionic acid. AHPA-Val was 6 times (IC50 = 1.2 micrograms/ml) as strong as bestatin (IC50 = 7.0 micrograms/ml) against

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