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56250

Sigma-Aldrich

trans-4-Hydroxy-L-proline

≥99.0% (NT), BioXtra

Sinônimo(s):

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

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About This Item

Fórmula empírica (Notação de Hill):
C5H9NO3
Número CAS:
Peso molecular:
131.13
Beilstein:
81441
Número CE:
Número MDL:
Código UNSPSC:
12352209
ID de substância PubChem:
NACRES:
NA.26

Nome do produto

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

linha de produto

BioXtra

Nível de qualidade

Ensaio

≥99.0% (NT)

Formulário

solid

atividade óptica

[α]20/D −76.0±1.5°, c = 5% in H2O

Impurezas

≤0.3% foreign amino acids

resíduo de ignição

≤0.1% (as SO4)

perda

≤0.1% loss on drying, 110 °C

cor

colorless to white

pf

273 °C (dec.) (lit.)

traços de ânion

chloride (Cl-): ≤100 mg/kg
sulfate (SO42-): ≤100 mg/kg

traços de cátion

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

aplicação(ões)

peptide synthesis

cadeia de caracteres 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

chave InChI

PMMYEEVYMWASQN-DMTCNVIQSA-N

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Ações bioquímicas/fisiológicas

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.

Outras notas

Natural constituent of animal structural proteins such as collagen and elastin.
Enzymes and intermediates of hydroxyproline degradation

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 1

Equipamento de proteção individual

Eyeshields, Gloves, type N95 (US)


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E. Adams
Methods in Enzymology, 17B, 266-266 (1971)
Shahrzad Hosseininia et al.
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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
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
Mari Ogawa-Ohnishi et al.
Nature chemical biology, 9(11), 726-730 (2013-09-17)
Hydroxyproline (Hyp) O-arabinosylation is a post-translational modification that is prominent in extracellular glycoproteins in plants. Hyp O-arabinosylation is generally found in these glycoproteins in the form of linear oligoarabinoside chains and has a key role in their function by contributing
Massimo Petrera et al.
Arthroscopy : the journal of arthroscopic & related surgery : official publication of the Arthroscopy Association of North America and the International Arthroscopy Association, 29(10), 1685-1692 (2013-10-01)
This study aimed to determine the effects of platelet-rich plasma (PRP) on the histologic, biochemical, and biomechanical properties of tissue-engineered cartilage. Chondrocytes isolated from bovine metacarpal-phalangeal articular cartilage were seeded on top of a porous ceramic substrate (calcium polyphosphate [CPP]).

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