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H5877

Sigma-Aldrich

cis-4-Hydroxy-D-proline

Synonym(s):
D-allo-Hydroxyproline, (2R,4R)-(+)-4-Hydroxy-2-pyrrolidinecarboxylic acid
Empirical Formula (Hill Notation):
C5H9NO3
CAS Number:
Molecular Weight:
131.13
Beilstein:
81439
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.26

assay

≥98% (TLC)

Quality Level

form

powder

technique(s)

ligand binding assay: suitable

color

white

mp

243 °C (dec.) (lit.)

application(s)

peptide synthesis

SMILES string

O[C@H]1CN[C@H](C1)C(O)=O

InChI

1S/C5H9NO3/c7-3-1-4(5(8)9)6-2-3/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4-/m1/s1

InChI key

PMMYEEVYMWASQN-QWWZWVQMSA-N

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Packaging

250 mg in poly bottle
1, 10 g in poly bottle

Biochem/physiol Actions

Cis-4-Hydroxy-D-proline may be used as a starting material for the 13-step synthesis of new conformationally restricted PNA adenine monomer and the synthesis of N-Benzyl pyrrolidinyl sordaricin derivatives. Cis-4-Hydroxy-D-proline is a substrate that may be used to study the specificity and kinetics of D-alanine dehydrogenase. Cis-4-Hydroxy-D-proline may be used to analyze the substrate specificity of amino acid transporter PAT1.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. H5877.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Storage Class Code

13 - Non 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

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

A Püschl et al.
Organic letters, 2(26), 4161-4163 (2001-01-11)
[reaction:see text] A new conformationally restricted PNA adenine monomer has been synthesized in 13 steps from cis-4-hydroxy-D-proline. A fully modified adenine decamer displayed improved binding affinity toward complementary DNA and RNA oligonucleotides as compared to that of the parent PNA
Masami Arai et al.
Bioorganic & medicinal chemistry letters, 12(19), 2733-2736 (2002-09-10)
N-Benzyl pyrrolidinyl sordaricin derivatives have been synthesized from cis-4-hydroxy-D-proline in a stereocontrolled manner. These compounds maintained moderate antifungal activity against several pathogenic fungal strains. Their MIC values against Candida albicans were in the range of 0.25-2 microg/mL.
Charles E Deutch
FEMS microbiology letters, 238(2), 383-389 (2004-09-11)
3,4-Dehydro-DL-proline is a toxic analogue of L-proline which has been useful in studying the uptake and metabolism of this key amino acid. When membrane fractions from Escherichia coli strain UMM5 (putA1::Tn5 proC24) lacking both L-proline dehydrogenase and L-Delta(1)-pyrroline-5-carboxylate reductase were
L Metzner et al.
Amino acids, 31(2), 111-117 (2006-05-16)
The proton coupled amino acid transporter PAT1 expressed in intestine, brain, and other organs accepts L- and D-proline, glycine, and L-alanine but also pharmaceutically active amino acid derivatives such as 3-amino-1-propanesulfonic acid, L-azetidine-2-carboxylic acid, and cis-4-hydroxy-D-proline as substrates. We systematically
Ashley C Campbell et al.
Archives of biochemistry and biophysics, 698, 108727-108727 (2020-12-18)
Proline utilization A (PutA) proteins are bifunctional proline catabolic enzymes that catalyze the 4-electron oxidation of l-proline to l-glutamate using spatially-separated proline dehydrogenase and l-glutamate-γ-semialdehyde dehydrogenase (GSALDH, a.k.a. ALDH4A1) active sites. The observation that l-proline inhibits both the GSALDH activity

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