Hybrid SCFA-hydroxyl-derivatized monosaccharides, methods of synthesis, and methods of treating disorders

A compound of formula II or formula IV, or a pharmaceutically acceptable salt thereof:

• or
• wherein,
• R4 is H and each of R1, R2 and R3 is —C(O)(CH2)2CH3;
• and
• R is alkyl, alkenyl or alkyne, each of which is optionally substituted with 1-4 substituents selected from acyl, oxo, azido, aryl, halogen, —OC(O)alkyl, or —SC(O)alkyl.

A compound of formula III, or a pharmaceutically acceptable salt thereof:

• wherein,
• R4 is H and each of R1, R2 and R3 is —C(O)(CH2)2CH3;
• and
• R is alkyl, alkenyl or alkyne, each of which is optionally substituted with 1-4 substituents selected from acyl, oxo, azido, aryl, halogen, —OC(O)alkyl, or —SC(O)alkyl.

A method for increasing production of a recombinant glycoprotein in a cell, the method comprising the step of contacting said cell with a compound of formula I, or pharmaceutically acceptable salt thereof:

• wherein,
• R4 is H and each of R1, R2 and R3 is independently —C(O)(CH2)nCH3 wherein each n is independently an integer from 1-18;
• and
• R is alkyl, alkenyl or alkyne, each of which is optionally substituted with 1-4 substituents selected from acyl, oxo, azido, aryl, halogen, —OC(O)alkyl, or —SC(O)alkyl,
• in an amount sufficient to increase recombinant glycoprotein biosynthesis in said cell, thereby increasing production of a recombinant glycoprotein in said cell.

A method of incorporating a compound of formula I, or pharmaceutically acceptable salt thereof:

• wherein,
• R4 is H and each of R1, R2 and R3 is independently —C(O)(CH2)nCH3 wherein each n is independently an integer from 1-18;
• and
• R is alkyl, alkenyl or alkyne, each of which is optionally substituted with 1-4 substituents selected from acyl, oxo, azido, aryl, halogen, —OC(O)alkyl, or —SC(O)alkyl,
• in a glycan cell surface or in a glycosylation pathway comprising introducing the compound to a recombinant glycoprotein production process, wherein toxicity of said glycoprotein is reduced as compared to an appropriate control.

A method of incorporating a compound of formula I, or pharmaceutically acceptable salt thereof:

• wherein,
• R4 is H and each of R1, R2 and R3 is independently —C(O)(CH2)nCH3 wherein each n is independently an integer from 1-18;
• and
• R is alkyl, alkenyl or alkyne, each of which is optionally substituted with 1-4 substituents selected from acyl, oxo, azido, aryl, halogen, —OC(O)alkyl, or —SC(O)alkyl,
• in a glycan cell surface or in a glycosylation pathway comprising introducing the compound to a recombinant glycoprotein production process, wherein toxicity of said glycoprotein is absent.

A method of incorporating a compound of formula I, or pharmaceutically acceptable salt thereof:

• wherein,
• R4 is H and each of R1, R2 and R3 is independently —C(O)(CH2)nCH3 wherein each n is independently an integer from 1-18;
• and
• R is alkyl, alkenyl or alkyne, each of which is optionally substituted with 1-4 substituents selected from acyl, oxo, azido, aryl, halogen, —OC(O)alkyl, or —SC(O)alkyl,
• in a glycan cell surface or in a glycosylation pathway comprising introducing the compound to a biosynthesis pathway, wherein toxicity is reduced as compared to an appropriate control.

A method of incorporating a compound of formula I, or pharmaceutically acceptable salt thereof:

• wherein,
• R4 is H and each of R1 R2 and R3 is independently —C(O)(CH2)nCH3 wherein each n is independently an integer from 1-18;
• and
• R is alkyl, alkenyl or alkyne, each of which is optionally substituted with 1-4 substituents selected from acyl, oxo, azido, aryl, halogen, —OC(O)alkyl, or —SC(O)alkyl,
• in a glycan cell surface or in a glycosylation pathway comprising introducing the compound to a biosynthesis pathway, wherein toxicity is absent.