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I9759

Sigma-Aldrich

Ile-Pro-Ile

≥97% (HPLC)

Synonym(s):

Diprotin A

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About This Item

Empirical Formula (Hill Notation):
C17H31N3O4
CAS Number:
90614-48-5
Molecular Weight:
341.45
MDL number:
MFCD00038707
UNSPSC Code:
51111800
PubChem Substance ID:
24896160
NACRES:
NA.77

Assay

≥97% (HPLC)

form

powder

solubility

water: 1 mg/mL, clear, colorless

storage temp.

−20°C

SMILES string

CCC(C)C(N)C(=O)N1CCCC1C(=O)NC(C(C)CC)C(O)=O

InChI

1S/C17H31N3O4/c1-5-10(3)13(18)16(22)20-9-7-8-12(20)15(21)19-14(17(23)24)11(4)6-2/h10-14H,5-9,18H2,1-4H3,(H,19,21)(H,23,24)

InChI key

JNTMAZFVYNDPLB-UHFFFAOYSA-N

Amino Acid Sequence

Ile-Pro-Ile

Application

Ile-Pro-Ile has been used as a supplement for blood collection for hormone measurement and used in Islets cell culture to stabilize glucagon-like peptide-1 (GLP-1). It has also been used to inhibit the breakdown of gonadotropin-inhibitory hormone (GnIH) following serum collection.

Biochem/physiol Actions

Inhibitor of dipeptidyl peptidase IV. Inhibits entry of HIV-1 or HIV-2 into T lymphoblastoid and monocytoid cell lines.

Features and Benefits

This compound is featured on the Neuropeptidases page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class Code

11 - 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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Carlos García-Aparicio et al.
Journal of medicinal chemistry, 49(17), 5339-5351 (2006-08-18)
Here we describe a novel type of enzyme-based prodrug approach in which a dipeptide moiety is linked to a nonpeptidic therapeutic drug through an amide bond which is specifically cleaved by the dipeptidyl-peptidase IV (DPP IV/CD26) enzyme activity present in
Preeshila Behary et al.
Diabetes care, 42(8), 1446-1453 (2019-06-10)
Roux-en-Y gastric bypass (RYGB) augments postprandial secretion of glucagon-like peptide 1 (GLP-1), oxyntomodulin (OXM), and peptide YY (PYY). Subcutaneous infusion of these hormones ("GOP"), mimicking postprandial levels, reduces energy intake. Our objective was to study the effects of GOP on
Pancreatic alpha cell-derived glucagon-related peptides are required for beta cell adaptation and glucose homeostasis
Traub S, et al.
Cell Reports, 18(13), 3192-3203 (2017)
Gemma Pujadas et al.
Molecular metabolism, 39, 101008-101008 (2020-05-12)
Glucose-dependent insulinotropic polypeptide (GIP) conveys information from ingested nutrients to peripheral tissues, signaling energy availability. The GIP Receptor (GIPR) is also expressed in the bone marrow, notably in cells of the myeloid lineage. However, the importance of gain and loss
Effect of gonadotropin-inhibitory hormone on luteinizing hormone secretion in humans
George JT, et al.
Clinical Endocrinology, 86(5), 731-738 (2017)
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