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56250

trans-4-Hydroxy-L-proline

Name: <I>trans</I>-4-Hydroxy-<SC>L</SC>-proline
Brand: SIGMA

≥99.0% (NT), BioXtra

Synonym(s):

(2S,4R)-4-Hydroxypyrrolidine-2-carboxylic acid, Hyp

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About This Item

Empirical Formula (Hill Notation):

C₅H₉NO₃

CAS Number:

51-35-4

Molecular Weight:

131.13

NACRES:

NA.26

PubChem Substance ID:

57651574

UNSPSC Code:

12352209

EC Number:

200-091-9

MDL number:

MFCD00064320

Beilstein/REAXYS Number:

81441

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Product Name

trans-4-Hydroxy-L-proline, BioXtra, ≥99.0% (NT)

product line

BioXtra

Quality Level

100

assay

≥99.0% (NT)

form

solid

optical activity

[α]20/D −76.0±1.5°, c = 5% in H₂O

impurities

≤0.3% foreign amino acids

ign. residue

≤0.1% (as SO₄)

loss

≤0.1% loss on drying, 110 °C

color

colorless to white

mp

273 °C (dec.) (lit.)

anion traces

chloride (Cl^-): ≤100 mg/kg, sulfate (SO₄^2-): ≤100 mg/kg

cation traces

Ca: ≤10 mg/kg, Cd: ≤5 mg/kg, Co: ≤5 mg/kg, Cr: ≤5 mg/kg, Cu: ≤5 mg/kg, Fe: ≤5 mg/kg, K: ≤50 mg/kg, Mg: ≤5 mg/kg, Mn: ≤5 mg/kg, NH₄⁺: ≤100 mg/kg, Na: ≤50 mg/kg, Ni: ≤5 mg/kg, Pb: ≤5 mg/kg, Zn: ≤5 mg/kg

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-DMTCNVIQSA-N

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Related Categories

Amino Acids, Resins & Reagents for Peptide Synthesis

Biochemicals

Cell Culture Supplements & Reagents

High-Purity Biochemicals and Reagents

Building Blocks, Resins, and Coupling Reagents for GLP-1 Synthesis

Biochem/physiol Actions

Trans-4-Hydroxy-L-proline is used as a starting material in the synthesis of (-)-secrinine; the synthesis of prolinol-based nucleotide analogues with N-phosphonomethyl moiety attached to the nitrogen atom of prolinol ring and in asymmetric synthesis of the ABC-ring system of the antitumor antibiotic MPC1001.

Trans-4-Hydroxy-L-proline is used in the organic synthesis of depsilairdin analogues, noncompetitive peptidomimetic inhibitors of multidrug resistance P-glycoprotein and 3-guaninyl-5-hydroxymethyl-2-pyrrolidinone (4) or 3-adeninyl-5-hydroxymethyl-2-pyrrolidinone (5) nucleoside analogues.

Other Notes

Enzymes and intermediates of hydroxyproline degradation

Natural constituent of animal structural proteins such as collagen and elastin.

Storage Class

11 - Combustible Solids

wgk

WGK 1

ppe

Eyeshields, Gloves, type N95 (US)

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E. Adams

Methods in Enzymology, 17B, 266-266 (1971)

Hydroxyproline content of needle biopsies as an objective measure of liver fibrosis: Emphasis on sampling variability.

Hsuan-Shu Lee et al.

Journal of gastroenterology and hepatology, 20(7), 1109-1114 (2005-06-16)

Needle liver biopsy is essential for the diagnosis of liver fibrosis and cirrhosis. However, sampling variability has been reported by semiquantitative methods. The aim of the present study was to investigate quantitatively the sampling variability of needle liver biopsy on

The effect of hypoxia on the chondrogenic differentiation of co-cultured articular chondrocytes and mesenchymal stem cells in scaffolds.

Ville V Meretoja et al.

Biomaterials, 34(17), 4266-4273 (2013-03-16)

In this work, we investigated the effects of lowered oxygen tension (20% and 5% O2) on the chondrogenesis and hypertrophy of articular chondrocytes (ACs), mesenchymal stem cells (MSCs) and their co-cultures with a 30:70 AC:MSC ratio. Cells were cultured for

Cartilage collagen damage in hip osteoarthritis similar to that seen in knee osteoarthritis; a case-control study of relationship between collagen, glycosaminoglycan and cartilage swelling.

Shahrzad Hosseininia et al.

BMC musculoskeletal disorders, 14, 18-18 (2013-01-11)

It remains to be shown whether OA shares molecular similarities between different joints in humans. This study provides evidence for similarities in cartilage molecular damage in osteoarthritic (OA) joints. Articular cartilage from osteoarthritic hip joints were analysed and compared to

Dual mechanism of zinc-proline catalyzed aldol reactions in water.

Jacob Kofoed et al.

Chemical communications (Cambridge, England), (14)(14), 1482-1484 (2006-04-01)

The aldol reaction of acetone with aldehydes in aqueous medium under catalysis by zinc-proline (Zn(L-Pro)2) and secondary amines such as proline, (2S,4R)-4-hydroxyproline (Hyp) and (S)-(+)-1-(2-pyrrolidinomethyl)pyrrolidine (PMP) is shown to proceed by an enamine mechanism, as evidenced by reductive trapping of

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Global Trade Item Number

SKU	GTIN
56250-25G	04061833417300
56250-100G	04061833380888
56250-1G-KC	04061824803631
56250-5G	04061833356005

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