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151688

Sigma-Aldrich

L-Histidine

98%

Synonym(s):

(S)-2-Amino-3-(4-imidazolyl)propionic acid, NSC 137773

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About This Item

Empirical Formula (Hill Notation):
C6H9N3O2
CAS Number:
71-00-1
Molecular Weight:
155.15
Beilstein/REAXYS Number:
84088
EC Number:
200-745-3
MDL number:
MFCD00064315
UNSPSC Code:
12352103

assay

98%

optical activity

[α]23/D −38.4°, c = 3 in H2O

mp

282 °C (dec.) (lit.)

SMILES string

N[C@@H](Cc1c[nH]cn1)C(O)=O

InChI

1S/C6H9N3O2/c7-5(6(10)11)1-4-2-8-3-9-4/h2-3,5H,1,7H2,(H,8,9)(H,10,11)/t5-/m0/s1

InChI key

HNDVDQJCIGZPNO-YFKPBYRVSA-N

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Biochem/physiol Actions

Precursor of histamine by action of histidine decarboxylase.

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Certificates of Analysis (COA)

Lot/Batch Number
05024KV
12529MZ
04821JR
04713EQ
27330AO

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Marie-Rose Abdo et al.
Bioorganic & medicinal chemistry letters, 19(9), 2440-2443 (2009-04-07)
Activation of the human carbonic anhydrase (CA, EC 4.2.1.1) isozymes I, II (cytosolic) and IX (transmembrane, tumor-associated isoform) with a series of arylsulfonylhydrazido-l-histidines incorporating 4-substituted-phenyl, pentafluorophenyl- and beta-naphthyl moieties was investigated. The compounds showed a weak hCA I activation profile
Claudia Temperini et al.
Bioorganic & medicinal chemistry letters, 16(19), 5152-5156 (2006-07-28)
The X-ray crystallographic structure for the adduct of an activator with human carbonic anhydrase isozyme I (hCA I) is reported. L-Histidine binds deep within the enzyme active site, participating in a network of hydrogen bonds involving its carboxylate moiety and
Claudia Temperini et al.
Bioorganic & medicinal chemistry letters, 15(23), 5136-5141 (2005-10-11)
Activation of the carbonic anhydrase (CA, EC 4.2.1.1) isoforms hCA I, II, and IV with l-histidine and some of its derivatives has been investigated by kinetic and X-ray crystallographic methods. l-His was a potent activator of isozymes I and IV
Alessio Innocenti et al.
Bioorganic & medicinal chemistry letters, 19(13), 3430-3433 (2009-05-26)
An activation study of the membrane-associated carbonic anhydrase (CA, EC 4.2.1.1) isoform XV with a series of natural and non-natural amino acids and aromatic/heterocyclic amines is reported. Murine CA XV was strongly activated by some amino acids (d-Phe, l-/d-DOPA, d-Trp
Daniela Vullo et al.
Bioorganic & medicinal chemistry letters, 18(15), 4303-4307 (2008-07-17)
An activation study of the human carbonic anhydrase (hCA, EC 4.2.1.1) isoforms hCA III (cytosolic) and IV (membrane-associated) with a series of natural and non-natural amino acids and aromatic/heterocyclic amines is reported. hCA III was efficiently activated by d-His, serotonin
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Chromatograms

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