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H15403

Sigma-Aldrich

L-Histidine methyl ester dihydrochloride

97%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C7H11N3O2 · 2HCl
CAS Number:
7389-87-9
Molecular Weight:
242.10
Beilstein:
3572009
EC Number:
230-973-9
MDL number:
MFCD00012701
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
24895465
NACRES:
NA.22

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 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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3-Methyl-L-histidine

Sigma-Aldrich

M9005

3-Methyl-L-histidine

Histidine European Pharmacopoeia (EP) Reference Standard

H0750000

Histidine

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
Xiaoyu Su et al.
Chirality, 21(5), 539-546 (2008-08-14)
Two kinds of novel chiral molecular tweezers containing imidazoliums were synthesized from L-alanine, L-phenylalanine, and L-glutamic acid. They are constructed by the chiral imidazolium pincers and two different spacers which are 1,3-bis (bromomethyl)benzene and 2,6-bis(bromomethyl)pyridine, respectively. The enantioselective recognition of
Novel metal-chelate affinity sorbents for reversible use in catalase adsorption
Akgol S and Denizli A
Journal of Molecular Catalysis. B, Enzymatic, 28(1), 7-14 (2004)
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