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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:
1722350
MDL number:
MFCD00010516
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
24895609
NACRES:
NA.26

product name

DL-3-Hydroxynorvaline, ≥98% (TLC)

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

Signal Word

Danger

Hazard Statements

H315,H318,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

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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F A Barile et al.
Archives of biochemistry and biophysics, 270(1), 294-301 (1989-04-01)
Amino acid substitutions in collagen that impair folding of the triple helix result in significant increases in intracellular degradation of newly synthesized collagen. We have studied the effects of agents that cause other kinds of defects in collagen: hydroxynorvaline, a
Y J Gordon et al.
Current eye research, 5(2), 93-99 (1986-02-01)
The present study examined the anti-herpetic effect of the glycoprotein inhibitors, hydroxynorvaline and 2-deoxyglucose, alone and in combination with trifluridine on murine ocular herpes. Following ocular inoculation with a large dose of HSV-1 RE strain (10(6) pfu), ICR mice were
G Hortin et al.
The Journal of biological chemistry, 255(15), 7051-7054 (1980-08-10)
The proteolytic processing of rat pre-prolactin (Pre-Prl) to prolactin in isolated hemipituitaries was inhibited by the threonine analog, beta-hydroxynorvaline (Hnv). Pre-Prl accumulated as a major labeled intracellular product, even during pulse labeling longer than 2 h, but it was not
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
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.
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