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Key Documents

441562

Sigma-Aldrich

trans-1-Acetyl-4-hydroxy-L-proline

≥98%, for peptide synthesis

Synonym(s):

N-Acetyl-L-hydroxyproline

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About This Item

Empirical Formula (Hill Notation):
C7H11NO4
CAS Number:
Molecular Weight:
173.17
Beilstein:
84043
EC Number:
MDL number:
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.22

product name

trans-1-Acetyl-4-hydroxy-L-proline, ≥98%

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

SMILES string

CC(=O)N1C[C@H](O)C[C@H]1C(O)=O

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

InChI key

BAPRUDZDYCKSOQ-RITPCOANSA-N

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).

Pictograms

Corrosion

Signal Word

Danger

Hazard Statements

Precautionary Statements

Hazard Classifications

Eye Dam. 1

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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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)
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)
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)
[Action of N-acetyl-hydroxyproline in the treatment of cutaneous ulcerative lesions].
C Famulari et al.
Annali italiani di chirurgia, 51(5), 527-536 (1979-01-01)
Thi Mai Hoa Bach et al.
Applied microbiology and biotechnology, 97(1), 247-257 (2012-06-19)
The proline analogue cis-4-hydroxy-L-proline (CHOP), which inhibits the biosynthesis of collagen, has been clinically evaluated as an anticancer drug, but its water solubility and low molecular weight limits its therapeutic potential since it is rapidly excreted. In addition, CHOP is

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