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294357

Sigma-Aldrich

DL-Homophenylalanine

98%

Synonym(s):

(±)-2-Amino-4-phenylbutyric acid

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About This Item

Linear Formula:
C6H5(CH2CH2)CH(NH2)CO2H
CAS Number:
1012-05-1
Molecular Weight:
179.22
MDL number:
MFCD00063092
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
24857709
NACRES:
NA.22

Assay

98%

reaction suitability

reaction type: solution phase peptide synthesis

mp

282 °C (dec.) (lit.)

application(s)

peptide synthesis

SMILES string

NC(CCc1ccccc1)C(O)=O

InChI

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

InChI key

JTTHKOPSMAVJFE-UHFFFAOYSA-N

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Related Categories

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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Kento Koketsu et al.
Applied and environmental microbiology, 79(7), 2201-2208 (2013-01-29)
L-Homophenylalanine (L-Hph) is a useful chiral building block for synthesis of several drugs, including angiotensin-converting enzyme inhibitors and the novel proteasome inhibitor carfilzomib. While the chemoenzymatic route of synthesis is fully developed, we investigated microbial production of L-Hph to explore
D Sobolewski et al.
The journal of peptide research : official journal of the American Peptide Society, 65(4), 465-471 (2005-04-09)
In continuation of our efforts to elucidate the role of positions 2 and 3 in arginine vasopressin (AVP) and its analogues, we designed and synthesized peptides modified in these positions with l-beta-homophenylalanine (beta-Hph). Two of them had just this single
S R Syam Prakash et al.
Journal of plant physiology, 163(11), 1135-1149 (2006-05-24)
Calcium-dependent protein kinases (CPKs) play important roles in multiple signal transduction pathways but the precise role of individual CPK is largely unknown. We isolated two cDNAs encoding two CPK isoforms (Cicer arietinum CPKs-CaCPK1 and CaCPK2) of chickpea. Their expression in
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
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
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