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Nim-Trityl-D-histidine methyl ester hydrochloride

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Category

D-Amino Acids

Catalog number

BAT-003539

CAS number

200927-02-2

Molecular Formula

C26H25N3O2·HCl

Molecular Weight

448.00

Nim-Trityl-D-histidine methyl ester hydrochloride

Specification
Reference Reading

IUPAC Name

methyl (2R)-2-amino-3-(1-tritylimidazol-4-yl)propanoate;hydrochloride

Synonyms

D-His(Trt)-OMe HCl; methyl (2R)-2-amino-3-(1-tritylimidazol-4-yl)propanoate hydrochloride; (R)-Methyl 2-amino-3-(1-trityl-1H-imidazol-4-yl)propanoate hydrochloride

Appearance

White powder

Purity

≥ 99% (TLC)

Storage

Store at 2-8 °C

InChI

InChI=1S/C26H25N3O2.ClH/c1-31-25(30)24(27)17-23-18-29(19-28-23)26(20-11-5-2-6-12-20,21-13-7-3-8-14-21)22-15-9-4-10-16-22;/h2-16,18-19,24H,17,27H2,1H3;1H/t24-;/m1./s1

InChI Key

RSIWDQDVADNDKT-GJFSDDNBSA-N

Canonical SMILES

COC(=O)C(CC1=CN(C=N1)C(C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4)N.Cl

1. L-histidine methyl ester dihydrochloride

V H Vilchiz, R E Norman, S C Chang Acta Crystallogr C. 1996 Mar 15;52 ( Pt 3):696-8. doi: 10.1107/s0108270195013308.

The title compound, C7H13N3O2(2+).2Cl-, has distances and angles quite similar to those of histidine hydrochloride monohydrate [Donohue & Caron (1964). Acta Cryst. 17, 1178-1180], except for the distances within the ester functionality.

2. Asymmetric Total Synthesis of Griseofamine B and Its Three Stereoisomers

Tao Sheng, Caiyun Ma, Guangyan Zhang, Xuan Pan, Zhanzhu Liu J Nat Prod. 2022 Apr 22;85(4):1128-1133. doi: 10.1021/acs.jnatprod.2c00069. Epub 2022 Mar 3.

The first total synthesis of griseofamine B is described starting from l-4-bromo tryptophan methyl ester hydrochloride via five steps and in 18% overall yield. Its three stereoisomers were also synthesized following the same procedure with the yields of 5%, 19%, and 5%, respectively. In vitro antibacterial activities were also evaluated. All four compounds exhibited less potent activity than griseofamine A.