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544051

Sigma-Aldrich

L-Homophenylalanine hydrochloride

97%

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About This Item

Linear Formula:
C6H5CH2CH2CH(NH2)CO2H · HCl
CAS Number:
21176-60-3
Molecular Weight:
215.68
MDL number:
MFCD03427064
UNSPSC Code:
12352209
PubChem Substance ID:
24878289
NACRES:
NA.22

Quality Level

100

Assay

97%

optical activity

[α]20/D +38°, c = 1 in 3 M HCl

reaction suitability

reaction type: solution phase peptide synthesis

mp

262-265 °C (dec.) (lit.)

application(s)

peptide synthesis

SMILES string

Cl.N[C@@H](CCc1ccccc1)C(O)=O

InChI

1S/C10H13NO2.ClH/c11-9(10(12)13)7-6-8-4-2-1-3-5-8;/h1-5,9H,6-7,11H2,(H,12,13);1H/t9-;/m0./s1

InChI key

CHBMONIBOQCTCF-FVGYRXGTSA-N

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

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Lot/Batch Number
07628BO

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Hsueh-Hsia Lo et al.
Biotechnology progress, 25(6), 1637-1642 (2009-09-22)
L-Homophenylalanine (L-HPA) and N(6)-protected-2-oxo-6-amino-hexanoic acid (N(6)-protected-OAHA) can be used as building blocks for the manufacture of angiotensin-converting enzyme inhibitors. To synthesize L-HPA and N(6)-protected-OAHA simultaneously from 2-oxo-4-phenylbutanoic acid (OPBA) and N(6)-protected-L-lysine, several variants of Escherichia coli aspartate aminotransferase (AAT) were
Chao-Hung Kao et al.
Journal of biotechnology, 134(3-4), 231-239 (2008-03-18)
A dihydropyrimidinase gene (pydB) was cloned from the moderate thermophilic Brevibacillus agri NCHU1002 and expressed in Escherichia coli. The purified dihydropyrimidinase exhibited strict d-enantioselectivity for D,L-p-hydroxyphenylhydantoin and D,L-5-[2-(methylthio)ethyl]hydantoin, and non-enantiospecificity for D,L-homophenylalanylhydantoin (D,L-HPAH). The hydrolytic activity of PydB was enhanced
A L Ahmad et al.
Biotechnology advances, 27(3), 286-296 (2009-06-09)
Over the past decade, L-homophenylalanine is extensively used in the pharmaceutical industry as a precursor for production of angiotensin-converting enzyme (ACE) inhibitor, which possesses significant clinical application in the management of hypertension and congestive heart failure (CHF). A number of
Sonja Nordhoff et al.
Bioorganic & medicinal chemistry letters, 19(22), 6340-6345 (2009-10-17)
For a series of beta-homophenylalanine based inhibitors of dipeptidyl peptidase IV ADME properties were improved by the incorporation of amide replacements. These efforts led to a novel series of potent and selective inhibitors of DPP-4 that exhibit an attractive pharmacokinetic
Sonja Nordhoff et al.
Bioorganic & medicinal chemistry letters, 19(15), 4201-4203 (2009-06-12)
Modifications of DPP-4 inhibitor 5, that was discovered by structure based design, are described and structure-activity relationships discussed. With analogue 7k one of the most potent non-covalent inhibitors of DPP-4 reported to date (IC(50)=0.38nM) was discovered. X-ray structure of inhibitor
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