Saccharides, Nucleosides, Derivatives
13C, 2H, 15N, 18O Labeling

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High Mannose N-Glycans

Omicron Biochemicals, Inc., 115 South Hill Street, South Bend, IN 46617-2701

Cell-surface oligosaccharides appended to proteins and lipids are key binding epitopes in many critical biological processes, including bacterial infection, cell development and the immune response. Understanding these processes at the molecular level requires access to a wide range of oligosaccharides of known structure to support investigations of enzyme substrate binding and specificity, to screen for carbohydrate binding proteins, and to develop assays for enzymic activity. Omicron Biochemicals, Inc. was awarded Small Business Innovation Research (SBIR) grants by the National Institutes of Health (NIH) in 2013 and 2015 to increase the commercial availability of these oligosaccharides, thus facilitating progress in this field.

Omicron has focused on the synthesis of oligosaccharides derived from the parent high-mannose oligosaccharide (14-mer) that is transferred en-bloc to polypeptides during translation. During Phase I of our project, we pursued a "bottom-up" synthetic approach instead of a "top-down" approach to overcome the limitations of the latter. All five O-glycosidic linkages found in naturally occurring high-mannose N-glycans of human glycoproteins were constructed, leading to the preparation of thirty-two (32) oligosaccharides (3- to 6-mers) using a generalized chemical approach. During Phase I of this project, Omicron chemists developed robust synthetic protocols and gained knowledge, experience and technical know-how to extend the chemical space in a subsequent Phase II project.

As of May 2017, Omicron has made over 100 high-mannose N-glycans available for purchase on their website at www.omicronbio.com. Products range from simple mannobiose compounds to mannose nonasaccharides. Mannose oligosaccharides with one or two N-acetyl-glucosamine residues are available, as are mannose oligosaccharides with a mannose phosphate residue.

As Omicron continues to expand the variety of obtainable high-mannose N-glycans, methods will be developed to array this extensive library to support anticipated screening efforts by investigators in the glycoscience community.

In the following list of products, we omit the configurational symbol, the letter denoting ring size, and the locant of the anomeric carbons. All of the monosaccharide units are pyranose rings of the D-form with the anomeric carbon at C1.

Omicron
Catalog
Number
Product Name
DIS-010Manα-2Man
DIS-011Manα-3Man
DIS-012Manα-6Man
TRI-007Manα-2Manα-2Man
TRI-008Manα-2Manα-3Man
TRI-009Manα-2Manα-6Man
TRI-010Manα-3Manα-6Man
TRI-005Manα-6Manα-6Man
TRI-006Manα-3[Manα-6]Man
TRI-011Manα-4[Manα-6]Man
TET-016Manα-2Manα-2Manα-2Man
TET-004Manα-2Manα-2Manα-3Man
TET-006Manα-2Manα-2Manα-6Man
TET-005Manα-2Manα-3Manα-6Man
TET-007Manα-2Manα-6Manα-6Man
TET-010Manα-2Manα-3[Manα-6]Man
TET-009Manα-2Manα-6[Manα-3]Man
TET-011Manα-3Manα-6[Manα-3]Man
TET-019Manα-6Manα-6[Manα-3]Man
TET-008Manα-3[Manα-6]Manα-6Man
TET-015Manα-3[Manα-4][Manα-6]Man
PEN-007Manα-2Manα-2Manα-3[Manα-6]Man
PEN-003Manα-2Manα-3Manα-6[Manα-3]Man
PEN-015Manα-2Manα-6Manα-6[Manα-3]Man
PEN-008Manα-2Manα-3[Manα-6]Manα-6Man
PEN-002Manα-2Manα-6[Manα-3]Manα-6Man
PEN-005Manα-2Manα-3[Manα-2Manα-6]Man
PEN-006Manα-2Manα-3[Manα-3Manα-6]Man
PEN-004Manα-2Manα-3[Manα-6Manα-6]Man
PEN-012Manα-6Manα-4[Manα-6Manα-6]Man
PEN-001Manα-3[Manα-6]Manα-6[Manα-3]Man
HEX-003Manα-2Manα-2Manα-3[Manα-3Manα-6]Man
HEX-004Manα-2Manα-2Manα-3[Manα-6Manα-6]Man
HEX-011Manα-2Manα-3Manα-6[Manα-2Manα-3]Man
HEX-010Manα-2Manα-6Manα-6[Manα-2Manα-3]Man
HEX-001Manα-2Manα-3[Manα-2Manα-6]Manα-6Man
HEX-012Manα-2Manα-3[Manα-6]Manα-6[Manα-3]Man
HEX-014Manα-2Manα-6[Manα-3]Manα-6[Manα-3]Man
HEX-002Manα-3[Manα-6]Manα-6[Manα-2Manα-3]Man
OLI-005Manα-2Manα-2Manα-3[Manα-2Manα-3Manα-6]Man
OLI-006Manα-2Manα-2Manα-3[Manα-2Manα-6Manα-6]Man
OLI-010Manα-2Manα-2Manα-3[Manα-3[Manα-6]Manα-6]Man
OLI-012Manα-2Manα-3[Manα-2Manα-6]Manα-6[Manα-3]Man
OLI-007Manα-2Manα-3[Manα-6]Manα-6[Manα-2Manα-3]Man
OLI-013Manα-2Manα-6[Manα-3]Manα-6[Manα-2Manα-3]Man
OLI-014Manα-2Manα-3[Manα-2Manα-6]Manα-6[Manα-2Manα-3]Man
OLI-008Manα-2Manα-3[Manα-6]Manα-6[Manα-2Manα-2Manα-3]Man
OLI-015Manα-2Manα-6[Manα-3]Manα-6[Manα-2Manα-2Manα-3]Man
OLI-009Manα-2Manα-3[Manα-2Manα-6]Manα-6[Manα-2Manα-2Manα-3]Man
Mannose oligosaccharides with one α-Glc residue
TRI-030Glcα-3Manα-2Man
TET-047Glcα-3Manα-2Manα-2Man
PEN-027Glcα-3Manα-2Manα-3[Manα-6]Man
PEN-026Glcα-3Manα-3[Manα-3Manα-6]Man
PEN-025Glcα-3Manα-3[Manα-6Manα-6]Man
HEX-029Glcα-3Manα-2Manα-2Manα-3[Manα-6]Man
OLI-029Glcα-3Manα-2Manα-2Manα-3[Manα-3Manα-6]Man
OLI-030Glcα-3Manα-2Manα-2Manα-3[Manα-6Manα-6]Man
OLI-028Glcα-3Manα-2Manα-3[Manα-3[Manα-6]Manα-6]Man
Mannose oligosaccharides with one D-GlcNAc residue
TRI-015Manα-3Manβ-4GlcNAc
TRI-016Manα-6Manβ-4GlcNAc
TET-020Manα-2Manα-3Manβ-4GlcNAc
TET-021Manα-3Manα-6Manβ-4GlcNAc
TET-022Manα-6Manα-6Manβ-4GlcNAc
TET-018Manα-3[Manα-6]Manβ-4GlcNAc
PEN-017Manα-2Manα-2Manα-3Manβ-4GlcNAc
PEN-018Manα-2Manα-3Manα-6Manβ-4GlcNAc
PEN-019Manα-2Manα-6Manα-6Manβ-4GlcNAc
PEN-013Manα-3Manα-6[Manα-3]Manβ-4GlcNAc
PEN-014Manα-6Manα-6[Manα-3]Manβ-4GlcNAc
HEX-019Manα-2Manα-2Manα-3[Manα-6]Manβ-4GlcNAc
HEX-008Manα-2Manα-3Manα-6[Manα-3]Manβ-4GlcNAc
HEX-009Manα-2Manα-6Manα-6[Manα-3]Manβ-4GlcNAc
HEX-018Manα-2Manα-3[Manα-3Manα-6]Manβ-4GlcNAc
HEX-017Manα-2Manα-3[Manα-6Manα-6]Manβ-4GlcNAc
HEX-016Manα-2Manα-3[Manα-6]Manα-6Manβ-4GlcNAc
HEX-020Manα-2Manα-6[Manα-3]Manα-6Manβ-4GlcNAc
HEX-015Manα-3[Manα-6]Manα-6[Manα-3]Manβ-4GlcNAc
OLI-019Manα-2Manα-2Manα-3[Manα-3Manα-6]Manβ-4GlcNAc
OLI-020Manα-2Manα-2Manα-3[Manα-6Manα-6]Manβ-4GlcNAc
OLI-021Manα-2Manα-3[Manα-2Manα-6]Manα-6Manβ-4GlcNAc
OLI-026Manα-2Manα-2Manα-3[Manα-3[Manα-6]Manα-6]Manβ-4GlcNAc
Mannose oligosaccharides with two D-GlcNAc residues
TRI-019Manβ-4GlcNAcβ-4GlcNAc
TET-032Manα1-3Manβ-4GlcNAcβ-4GlcNAc
TET-031Manα1-6Manβ-4GlcNAcβ-4GlcNAc
PEN-023Manα-2Manα-3Manβ-4GlcNAcβ-4GlcNAc
PEN-016Manα-3[Manα-6]Manβ-4GlcNAcβ-4GlcNAc
HEX-013Manα-2Manα-2Manα-3Manβ-4GlcNAcβ-4GlcNAc
HEX-023Manα-2Manα-3Manα-6Manβ-4GlcNAcβ-4GlcNAc
HEX-024Manα-2Manα-6Manα-6Manβ-4GlcNAcβ-4GlcNAc
HEX-026Manα-2Manα-3[Manα-6]Manβ-4GlcNAcβ-4GlcNAc
HEX-028Manα-3Manα-6[Manα-3]Manβ-4GlcNAcβ-4GlcNAc
HEX-027Manα-6Manα-6[Manα-3]Manβ-4GlcNAcβ-4GlcNAc
HEX-025Manα-3[Manα-6]Manα-6Manβ-4GlcNAcβ-4GlcNAc
OLI-023Manα-2Manα-3[Manα-3Manα-6]Manβ-4GlcNAcβ-4GlcNAc
OLI-024Manα-2Manα-3[Manα-6Manα-6]Manβ-4GlcNAcβ-4GlcNAc
OLI-011Manα-2Manα-2Manα-3[Manα-3Manα-6]Manβ-4GlcNAcβ-4GlcNAc
OLI-018Manα-2Manα-2Manα-3[Manα-6Manα-6]Manβ-4GlcNAcβ-4GlcNAc
OLI-025Manα-2Manα-3[Manα-2Manα-6]Manα-6Manβ-4GlcNAcβ-4GlcNAc
OLI-016Manα-2Manα-2Manα-3[Manα-2Manα-3Manα-6]Manβ-4GlcNAcβ-4GlcNAc
OLI-017Manα-2Manα-2Manα-3[Manα-2Manα-6Manα-6]Manβ-4GlcNAcβ-4GlcNAc
Mannose oligosaccharides with one mannose phosphate residue (Man4P or Man6P)
DIS-020Man4Pα-6Man disodium salt
DIS-017Man6Pα-2Man disodium salt
DIS-018Man6Pα-3Man disodium salt
DIS-019Man6Pα-6Man disodium salt
TET-044Manα-2Manα-3[Man4Pα-6]Man disodium salt
TET-043Manα-2Manα-3[Man6Pα-6]Man disodium salt
TET-041Manα-6Manα-6[Man6Pα-3]Man disodium salt
TET-042Man6Pα-6Manα-6[Manα-3]Man disodium salt
PEN-022Manα-2Manα-2Manα-3[Man6Pα-6]Man disodium salt
PEN-021Manα-2Manα-3Manα-6[Man6Pα-3]Man disodium salt
PEN-020Manα-2Manα-3[Man6Pα-6Manα-6]Man disodium salt

This page is also available as a PDF document.

Please see our Compound Class Index for a list of all product classes.