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About This Item
Empirical Formula (Hill Notation):
C7H11NO4
CAS Number:
Molecular Weight:
173.17
NACRES:
NA.22
PubChem Substance ID:
eCl@ss:
32160406
UNSPSC Code:
12352209
EC Number:
251-780-6
MDL number:
Beilstein/REAXYS Number:
84043
Product Name
trans-1-Acetyl-4-hydroxy-L-proline, ≥98%
Quality Level
InChI key
BAPRUDZDYCKSOQ-RITPCOANSA-N
InChI
1S/C7H11NO4/c1-4(9)8-3-5(10)2-6(8)7(11)12/h5-6,10H,2-3H2,1H3,(H,11,12)/t5-,6+/m1/s1
SMILES string
CC(=O)N1C[C@H](O)C[C@H]1C(O)=O
assay
≥98%
form
powder
optical activity
[α]20/D −119°, c = 4 in H2O
reaction suitability
reaction type: solution phase peptide synthesis
mp
132-133 °C (dec.) (lit.)
application(s)
peptide synthesis
Application
trans-1-Acetyl-4-hydroxy-L-proline can be used:
- In the stereospecific synthesis of 4-fluoroglutamic acid.
- To synthesize molecular targets for von Hippel-Lindau (VHL) E3 ubiquitin ligase.
- As a precursor to synthesize pseudopoly(amino acids) such as poly(trans-4-hydroxy-4-acyl-L-proline ester) and a biodegradable polymer, poly(lactic acid-glycolic acid-4-hydroxyproline).
signalword
Danger
hcodes
Hazard Classifications
Eye Dam. 1
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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Structure-guided design and optimization of small molecules targeting the protein?protein interaction between the von Hippel?Lindau (VHL) E3 ubiquitin ligase and the hypoxia inducible factor (HIF) alpha subunit with in vitro nanomolar affinities.
Galdeano C, et al.
Journal of Medicinal Chemistry, 57(20), 8657-8663 (2014)
Synthesis and characterization of a novel biodegradable polymer poly (lactic acid?glycolic acid?4?hydroxyproline).
Duan J, et al.
Journal of Applied Polymer Science, 103(6), 3585-3590 (2007)
Pseudopoly (amino acids): A Study of the Synthesis and Characterization of Poly (trans-4-hydroxy-N-acyl-L-proline esters).
Kwon H Y and Langer R
Macromolecules, 22(8), 3250-3255 (1989)
Stereospecific syntheses of all four stereoisomers of 4-fluoroglutamic acid.
Hudlicky M.
Journal of Fluorine Chemistry, 60(2-3), 193-210 (1993)
[The interaction of oxaceprol and fluindione].
B Bannwarth et al.
Therapie, 45(2), 162-163 (1990-03-01)
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