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A9075

Sigma-Aldrich

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

Sinônimo(s):

(2S,3R)-AHPA

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About This Item

Fórmula empírica (Notação de Hill):
C10H13NO3 · HCl
Número CAS:
128223-55-2
Peso molecular:
231.68
Número MDL:
MFCD00274394
Código UNSPSC:
12352200
ID de substância PubChem:
24891224

forma

solid

temperatura de armazenamento

−20°C

cadeia de caracteres SMILES

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

chave InChI

OPVMPYQFOLATCK-RJUBDTSPSA-N

Ações bioquímicas/fisiológicas

(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.

Pictogramas

Exclamation mark
GHS07

Palavra indicadora

Warning

Frases de perigo

H315,H319,H335

Classificações de perigo

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

Órgãos-alvo

Respiratory system

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

dust mask type N95 (US), Eyeshields, Gloves

Certificados de análise (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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