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H4002

Sigma-Aldrich

DL-3-Hydroxynorvaline

≥98% (TLC)

Synonym(s):

HNV, α-Amino-β-hydroxyvaleric acid, 2-Amino-3-hydroxypentanoic acid, 3-Hydroxy-2-aminopentanoic acid, DL-β-Hydroxynorvaline

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About This Item

Empirical Formula (Hill Notation):
C5H11NO3
CAS Number:
2280-42-4
Molecular Weight:
133.15
Beilstein/REAXYS Number:
1722350
MDL number:
MFCD00010516
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
24895609
NACRES:
NA.26

product name

DL-3-Hydroxynorvaline, ≥98% (TLC)

Quality Level

200

assay

≥98% (TLC)

form

powder

color

white

application(s)

cell analysis

storage temp.

−20°C

SMILES string

CCC(O)C(N)C(O)=O

InChI

1S/C5H11NO3/c1-2-3(7)4(6)5(8)9/h3-4,7H,2,6H2,1H3,(H,8,9)

InChI key

LGVJIYCMHMKTPB-UHFFFAOYSA-N

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Biochem/physiol Actions

3-Hydroxynorvaline (HNV) is a microbial, α amino acid threonine analogue which has antiviral activity (herpes virus) and is toxic to mammalian cells (embryotoxic and teratogenic) presumably via incorporation into proteins. 3-Hydroxynorvaline may be used as an unnatural amino acid to study the fidelity of protein translation at the level of acyl-tRNA editing. 3-Hydroxynorvaline may also be used to study enzymes and molecules involved in threonine metabolism.

pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

Hazard Classifications

Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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R Kumarasamy et al.
Virology, 138(1), 156-161 (1984-10-15)
Treatment of HSV-infected BHK-21 cells with 5-10 mM of beta-hydroxynorvaline (Hnv), an analog of threonine which blocked attachment of oligosaccharides at the Asn-X-Thr sites, markedly inhibited the synthesis of all viral glycoproteins as well as the major capsid protein. However
Anand Minajigi et al.
Biochemistry, 50(6), 1101-1109 (2011-01-13)
In all living systems, the fidelity of translation is maintained in part by the editing mechanisms of aminoacyl-tRNA synthetases (ARSs). Some nonproteogenic amino acids, including β-hydroxynorvaline (HNV) are nevertheless efficiently aminoacylated and become incorporated into proteins. To investigate the basis
R Counis et al.
Pathologie-biologie, 35(8), 1147-1151 (1987-10-01)
In order to investigate the biosynthetic pathway of LH subunits, anterior pituitary cells were cultured in the presence of [35S]Met and polypeptides immunologically-related (i.r.) to the alpha and LH beta subunits were isolated from cells and media using specific antisera.
C Ramos et al.
Applied and environmental microbiology, 58(5), 1677-1682 (1992-05-01)
In this work, we isolated and characterized mutants that overproduce threonine from Saccharomyces cerevisiae. The mutants were selected for resistance to the threonine analog alpha-amino-beta-hydroxynorvalerate (hydroxynorvaline), and, of these, the ones able to excrete threonine to the medium were chosen.
R Louw et al.
Amino acids, 29(3), 207-212 (2005-08-06)
3-Hydroxynorvaline (HNV; 2-amino-3-hydroxypentanoic acid), a microbial L-threonine analogue, is toxic to mammalian cells and displays antiviral properties. In view of this, we investigated the toxicity and/or potential teratogenicity of HNV in developing chicken and mouse embryos. HNV was administered to
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