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cis-4-Hydroxy-D-proline

Name: <I>cis</I>-4-Hydroxy-<SC>D</SC>-proline
Brand: SIGMA

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

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):

C₅H₉NO₃

CAS Number:

2584-71-6

Molecular Weight:

131.13

NACRES:

NA.26

PubChem Substance ID:

24895713

UNSPSC Code:

12352209

EC Number:

219-963-5

MDL number:

MFCD00005252

Beilstein/REAXYS Number:

81439

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Properties

Product Name

cis-4-Hydroxy-D-proline,

assay

≥98% (TLC)

Quality Level

100

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

Description

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.

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This Item	H1637	H7750	A8054
Sigma-Aldrich H5877 cis-4-Hydroxy-D-proline	Sigma-Aldrich H1637 cis-4-Hydroxy-L-proline	Sigma-Aldrich H7750 DL-Histidine	Sigma-Aldrich A8054 D(−)-2-Amino-5-phosphonopentanoic acid
form powder	form powder	form powder	form powder
technique(s) ligand binding assay: suitable	technique(s) ligand binding assay: suitable	technique(s) ligand binding assay: suitable	technique(s) ligand binding assay: suitable
assay ≥98% (TLC)	assay ≥98% (TLC)	assay ≥99% (TLC)	assay ≥98% (TLC)
Quality Level 100	Quality Level 100	Quality Level 200	Quality Level 100
color white	color white to faint yellow	color -	color white
mp 243 °C (dec.) (lit.)	mp 257 °C (dec.) (lit.)	mp 273 °C (dec.) (lit.)	mp 245-246 °C

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Pyrrolidine PNA: a novel conformationally restricted PNA analogue.

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

Synthesis and evaluation of novel pyrrolidinyl sordaricin derivatives as antifungal agents.

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.

Substrate specificity of the amino acid transporter PAT1.

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

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Global Trade Item Number

SKU	GTIN
H5877-10G	04061832416519
H5877-250MG	04061833799888
H5877-1G	04061826059753

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