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01423

Sigma-Aldrich

N-Acetyl-D-penicillamine

for HPLC derivatization, ≥99.0% (T)

Synonym(s):

NAP, NAPA, N-Acetyl-3-mercapto-D-valine

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About This Item

Empirical Formula (Hill Notation):
C7H13NO3S
CAS Number:
15537-71-0
Molecular Weight:
191.25
Beilstein:
1724742
EC Number:
239-585-4
MDL number:
MFCD00078887
UNSPSC Code:
12352116
PubChem Substance ID:
329747269
NACRES:
NA.26

grade

for HPLC derivatization

Assay

≥99.0% (T)

form

powder or crystals

optical activity

[α]20/D +10±2°, c = 1% in ethanol

technique(s)

HPLC: suitable (derivatization)

color

white

mp

185-190 °C (dec.)

application(s)

peptide synthesis

SMILES string

CC(=O)N[C@@H](C(O)=O)C(C)(C)S

InChI

1S/C7H13NO3S/c1-4(9)8-5(6(10)11)7(2,3)12/h5,12H,1-3H3,(H,8,9)(H,10,11)/t5-/m0/s1

InChI key

MNNBCKASUFBXCO-YFKPBYRVSA-N

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Application

Chiral reagent for the precolumn derivatization of amino acids or amino alcohols; the diastereoisomers formed can be efficiently resolved by HPLC on conventional reversed-phase columns

Biochem/physiol Actions

N-Acetyl-D-penicillamine (NAP or NAPA), a thiol compound, is often used as a control molecule in studies involving nitric oxide donor molecules such as S-nitroso-N-acetyl-dl-penicillamine (SNAP) and sodium nitroprusside (SNP). N-acetyl-D-penicillamine (NAPA) is also used as a heavy metal chelator.

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Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Precautionary Statements

P302 + P352 - P305 + P351 + P338

Hazard Classifications

Eye Irrit. 2 - 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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Chao Qian et al.
Light, science & applications, 9, 59-59 (2020-04-28)
Optical logic operations lie at the heart of optical computing, and they enable many applications such as ultrahigh-speed information processing. However, the reported optical logic gates rely heavily on the precise control of input light signals, including their phase difference
Y Ivashko-Pachima et al.
Molecular psychiatry, 22(9), 1335-1344 (2017-01-25)
Activity-dependent neuroprotective protein (ADNP), vital for brain formation and cognitive function, is mutated in autism and linked to neurodegenerative/psychiatric diseases. An eight-amino-acid peptide snippet of ADNP, NAP (NAPVSIPQ), identified as a smallest active fragment, includes the SxIP microtubule (MT) end-binding
Edward C Jones-López et al.
PLoS medicine, 8(3), e1000427-e1000427 (2011-03-23)
Each year, 10%-20% of patients with tuberculosis (TB) in low- and middle-income countries present with previously treated TB and are empirically started on a World Health Organization (WHO)-recommended standardized retreatment regimen. The effectiveness of this retreatment regimen has not been
Swapnali Barde et al.
Proceedings of the National Academy of Sciences of the United States of America, 113(52), E8472-E8481 (2016-12-13)
Major depressive disorder (MDD) is a substantial burden to patients, families, and society, but many patients cannot be treated adequately. Rodent experiments suggest that the neuropeptide galanin (GAL) and its three G protein-coupled receptors, GAL1-3, are involved in mood regulation.
Geraldine Rodriguez et al.
Frontiers in human neuroscience, 12, 300-300 (2018-08-11)
Sexual behaviour is the result of an interplay between distinct neural inhibitory and excitatory mechanisms. Individual differences in sexual excitation and sexual inhibition are proposed to play an important role in the processes sustaining the regulation of sexual behaviour. While
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