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H15403

Sigma-Aldrich

L-Histidine methyl ester dihydrochloride

97%

Sinónimos:

(S)-Histidine methyl ester dihydrochloride, Methyl L-histidinate dihydrochloride

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About This Item

Fórmula empírica (notación de Hill):
C7H11N3O2 · 2HCl
Número de CAS:
7389-87-9
Peso molecular:
242.10
Beilstein/REAXYS Number:
3572009
EC Number:
230-973-9
MDL number:
MFCD00012701
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
24895465
NACRES:
NA.22

Quality Level

100

assay

97%

optical activity

[α]20/D +9.0°, c = 2 in H2O

reaction suitability

reaction type: solution phase peptide synthesis

color

white

mp

207 °C (dec.) (lit.)

application(s)

peptide synthesis

SMILES string

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

InChI

1S/C7H11N3O2.2ClH/c1-12-7(11)6(8)2-5-3-9-4-10-5;;/h3-4,6H,2,8H2,1H3,(H,9,10);2*1H/t6-;;/m0../s1

InChI key

DWAYENIPKPKKMV-ILKKLZGPSA-N

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Application

L-Histidine methyl ester dihydrochloride can be used as a reactant to synthesize:
  • Imidazopyridine derivatives by Pictet-Spegler reaction with different aldehydes.
  • A metal-chelating ligand, N-methacryloyl-(l)-histidine methyl ester by reacting with methacryloyl chloride.
  • Zwitterionic polypeptide derivative by amidation reaction with poly (α,β-L-aspartic acid).

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificados de análisis (COA)

Lot/Batch Number
MKCW4516
MKCQ7560
MKCM4499
MKCJ9626
MKCH6408

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3-Methyl-L-histidine

Sigma-Aldrich

M9005

3-Methyl-L-histidine

L-Histidina European Pharmacopoeia (EP) Reference Standard

H0750000

L-Histidina

L-Histidine dihydrochloride ≥99.0% (AT)

Sigma-Aldrich

53340

L-Histidine dihydrochloride

R Stupnicki et al.
Journal of steroid biochemistry, 28(6), 663-667 (1987-12-01)
Steroid derivatives containing histidine methyl ester (HME), instead of histamine, were prepared by mixed anhydride coupling. The derivatives were crystalline, and when labelled in microgram quantities by using Iodo-gen (exposure time 1 h) the yield of the immunoreactive fraction was
Xue-Li Geng et al.
The Journal of organic chemistry, 73(21), 8558-8562 (2008-10-11)
The low-molecular-weight and easily prepared N-thiobenzoyl 1-methyl-histidine methyl ester 3k was utilized to efficiently catalyze the kinetic resolution of racemic secondary alcohols. Comparison of the conformations of amide catalyst 3c and thioamide catalyst 3k was made to understand the origin
Borislav Kovacević et al.
The journal of physical chemistry. A, 109(37), 8329-8335 (2006-07-13)
Gas-phase H/D exchange experiments with CD3OD and D2O and quantum chemical ab initio G3(MP2) calculations were carried out on protonated histidine and protonated histidine methyl ester in order to elucidate their bonding and structure. The H/D exchange experiments show that
Scott Worley et al.
Proteins, 46(3), 321-329 (2002-02-09)
Histidine decarboxylase (HDC) from Lactobacillus 30a converts histidine to histamine, a process that enables the bacteria to maintain the optimum pH range for cell growth. HDC is regulated by pH; it is active at low pH and inactive at neutral
T A Alston et al.
Biochemistry, 26(13), 4082-4085 (1987-06-30)
L-Histidine methyl ester inactivates histidine decarboxylase in a time-dependent manner. The possibility was considered that an irreversible reaction between enzyme and inhibitor occurs [Recsei, P. A., & Snell, E. E. (1970) Biochemistry 9, 1492-1497]. We have confirmed time-dependent inactivation by
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