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H5877

Sigma-Aldrich

cis-4-Hydroxy-D-proline

≥98% (TLC), suitable for ligand binding assays

Synonyme(s) :

(2R,4R)-(+)-4-Hydroxy-2-pyrrolidinecarboxylic acid, D-allo-Hydroxyproline

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About This Item

Formule empirique (notation de Hill):
C5H9NO3
Numéro CAS:
2584-71-6
Poids moléculaire :
131.13
Numéro Beilstein :
81439
Numéro CE :
219-963-5
Numéro MDL:
MFCD00005252
Code UNSPSC :
12352209
ID de substance PubChem :
24895713
Nomenclature NACRES :
NA.26

product name

cis-4-Hydroxy-D-proline,

Pureté

≥98% (TLC)

Forme

powder

Technique(s)

ligand binding assay: suitable

Couleur

white

Pf

243 °C (dec.) (lit.)

Application(s)

peptide synthesis

Chaîne SMILES 

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

Clé InChI

PMMYEEVYMWASQN-QWWZWVQMSA-N

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Actions biochimiques/physiologiques

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

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Consulter la Bibliothèque de documents

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.
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
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
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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